Anna Pulley

Anna Pulley

RedEye's sex columnist

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  • Is the 'slow fizzle' an OK way to break up?

    April 3, 2015

    Dear Anna,

  • Quick and dirty sex advice: Spring 2015

    March 27, 2015

    Happy spring, folks. Here are some short advice questions and answers to get you sprung (or convince you to go back into hibernation, as it were). If you're hankering for more quick `n' dirties, read winter's edition at

  • How to talk about past sexual abuse with a new partner

    March 19, 2015

    Sex columnist Anna Pulley addresses sharing intimate information without scaring off your partner.

  • Help! I've fallen into the parent trap

    March 5, 2015

    Dear Anna,

  • How do I tell my partner about my strange fantasy life?

    February 26, 2015

    Dear Anna,

  • Help! I'm a cuddle monster in my sleep

    February 19, 2015

    Dear Anna,

  • Straight guy, gay urges and internalized homophobia

    February 12, 2015

    Sex columnist Anna Pulley encourages straight guys denying gay urges to think about their internalized homophobia.

  • Should I date outside my race?

    February 5, 2015

    Dear Anna,

  • How do I get over a dating slump?

    January 14, 2015

    Dear Anna,

  • Fellatio and the fairer sex

    January 6, 2015

    Dear Anna,

  • Quick and dirty advice: Winter edition

    December 18, 2014

    It’s almost officially winter, and that means it’s time for another round of quick and dirty advice—because the days are short, and so are our attention spans. If you missed fall’s edition, read it here.

  • Where do I find another M for an MMF threesome?

    December 4, 2014

    Dear Anna,

  • How do I tell girls I'm bisexual?

    December 4, 2014

    Dear Anna,

  • The casual girlfriend-turned cohabitator

    November 20, 2014

    Dear Anna,

  • Should I keep a blah winter boy- or girlfriend?

    November 13, 2014

    Dear Anna,

  • Is my boyfriend's new Tinder account totally innocent?

    October 30, 2014

    Dear Anna,

  • Am I a high-priced booty call?

    October 30, 2014

    Dear Anna,

  • My awesome, monogomous relationship isn't enough

    October 16, 2014

    Dear Anna,

  • Does my boyfriend want me, or a fantasy porn girl?

    October 2, 2014

    Dear Anna,

  • How to move on from a soft breakup

    September 24, 2014

    Dear Anna,

  • Quick and dirty advice: Fall edition

    September 18, 2014

    Happy fall, folks! It’s time for turning leaves, pumpkin spice lattes, and the fall edition of quick and dirty advice. If you’re jonesin for summer’s edition, read it here. Now tie your scarf on loosely and let’s rumble.

  • I hate being the one to initiate sex

    September 4, 2014

    Hi Anna,

  • Advice: Should I act on my same-sex crush?

    February 5, 2014

    I'm 29 years old and have always sort of felt like I was in a "grey area" sexually, not overwhelming attracted to girls (though I did notice them), but not overwhelmingly attracted to guys on a physical level either (in fact, of the guys I've dated, I've never felt any real physical kind of connection toward them. Before, I thought it was just because we were a bad match, but now I wonder). I've gotten crushes on both girls and guys before but just thought maybe I had the crushes on the girls because I was attracted to a quality of theirs (nice hair/friendly/outgoing/etc.). Lately, though, I've been wondering whether my feelings might actually be because I'm bi or gay. I've never been with a girl before, and, while I like guys, I feel sometimes like I'd be more "myself" around a girl. Problem is, my family is not someone I could ever come out to (they're a little on the judgmental side, to put it lightly) and I don't know how my friends would react. So right now, I'm feeling a little like the feelings I have (I've got a pretty decent crush on a friend of mine who's a girl) are kind of in my head or something.

  • Advice: How to deal with Instagram jealousy

    January 30, 2014

    Hi Anna, I started dating this guy, and though we weren't "official," it bothered me that one of his female Instagram followers was obsessed with him. He claims they've never met, but she put his full name with a heart in her profile. He won't block her either; am I wrong to be upset?--Social Media Ruins Lives

  • Advice: The breast question you've been waiting for

    January 15, 2014

    Why do women wear cleavage-baring shirts if you don't want us to stare at your breasts?--Want To Know

  • Advice: My family won't accept who I am

    December 30, 2013

    Dear Anna,

  • Quick and dirty sex advice: Winter edition

    December 19, 2013

    Bisexual phases, cuddling compromise, and holiday hookups with an ex

  • Advice: How to stop a serial texter

    December 11, 2013

    There's a girl I started seeing a few weeks ago and so far, so good—except for one small thing: She texts me all the time. At first it was cute, but now I find it's interrupting my daily flow and work. I should also say that I rarely text, except to make plans or in emergencies. What's the etiquette here? How do I tell her to calm down without coming off as a jerk? — Texting Neophyte

  • Advice: I hate it when my boyfriend cries

    December 4, 2013

    I feel like a jerk about this but I can’t stand it when my boyfriend cries. What do I do?-- Don’t Cry Me A River

  • Advice: How can you tell if someone is flirting with you?

    November 27, 2013

    Hi Anna,

  • Advice: My boyfriend is afraid of sex toys

    November 20, 2013

    Hi Anna. I have trouble orgasming when I’m with my boyfriend. When I’m alone I can get myself off without any problems. I thought it might help if we used a vibrator in bed, but when I brought it up, he got all weird and defensive. Is he insecure about a toy being better/more efficient than he is? I don’t really understand and it’s frustrating. How can I talk him into at least trying it?--Not Toying Around

  • Advice: Can I lovingly choke you?

    November 14, 2013

    I’m relatively new to BDSM and I just started a sexual relationship with a nice vanilla-in-bed bisexual girl who knows I'm leaving Chicago soon. As we were talking about what we like in bed, she offered to sub for me, but I had no idea how to get things moving. I came very close to blurting out “I would like to choke you in a gentle and loving manner.” This can't be right. Where to start?--Choked Up

  • Advice: Etiquette for gay wedding proposals

    November 6, 2013

    I'm a gay man in a serious relationship with my boyfriend. I'm thinking of popping the question soon (fairly certain he'll say yes!), but wonder if there's etiquette for proposing when it's two men? Should I get down on a knee? Years of social norms and "The Bachelor" have left me confused. -- Groom Worries

  • Advice: How do I make him invest more in our relationship?

    October 30, 2013

    I am wondering what I must do to make a relationship stronger. The story is that I met a person through another friend. I made my intentions known, but to no avail the first time. After a period of time, we met again, and this time he asked me to "play." I was ready the first time we met, so of course, I enjoyed the encounter. Now I have called him, and he has eventually called me back, which made my day. We have even seen each other since, but I seem to be the one who wants a lot more to come of this. He has his moments, but I am the more emotional one. How do I get him to invest more into our "friendship/relationship?" Please advise!--Wantin' More

  • Advice: Where do all the hot lesbians hang out?

    October 10, 2013

    Anna, how would you genuinely respond to a new acquaintance who asks in conversation, "So where do all the young, hawt, hip, femme, single lesbians hang out?" Mind you, the question is asked in person (not online or via text where the anonymity warrants a blow-off or obnoxious response)? "Hooters," I want to respond (which may be true). The question irritates me. I find it rude, shallow, obnoxious and superficial, and I would find it so if it came from a man and he was asking me regarding heterosexual women. Or, am I irritated BECAUSE it sounds so much like a man asking regarding hetero women?—Char

  • Advice: His fist pleases me more

    September 12, 2013

    I'm a single mom and had been out of the dating scene since my youngest (now 10) was born. I recently became involved with a man that introduced me to fisting. I have to admit, though, albeit strange and new, it was more pleasurable than his penis. I reached a more intense orgasm with his fist. Two-part question: Is fisting common or new? And why does he get mad at me after I've had a fist orgasm? It's not my fault his fist pleases me more. Thank you.

  • Advice: How long should intercourse last?

    August 27, 2013

    I read recently that the average length of time for intercourse is three minutes. I think most girls like sex for more than three minutes. But then other times my female friends complain about guys lasting too long (though I don’t know exactly how long “too long” is). Is there a sweet spot? What should I be aiming for here?--Three Minutes of Your Time

  • How to talk about safe sex with a new partner

    July 17, 2013

    I’ve been dating this guy for a few months now. We haven’t had the “what are we” talk, but I presume that we’re both sleeping with other people. (For the record, I’ve slept with one other person). This kind of “don’t ask, don’t tell” arrangement is OK in the short term, but I’m wondering how to bring up safe-sex practices without making it a big deal. It seems important to talk about these things, right?--Asking and Telling

  • Advice: Are group relationships the new fad?

    July 10, 2013

    OK, so are group relationships like the new fad in Chicago? I've heard people talking about them lately and noticed sections for them on dating websites. My bi-curious friend hooked up with a girl who is in a group relationship with that self-proclaimed sex expert. He's hot, but umm please. Are group relationships normal or is this just something self-proclaimed sex experts do with girls who are confused about their sexuality?

  • Advice: Can cheaters change?

    July 3, 2013

    The old saying goes, "once a cheater, always a cheater." I have the opportunity to date someone I'm really, really into and who is really, really into me. Trouble is, he was in a long-distance relationship several years ago in which he cheated on his girlfriend multiple times. Mutual friends of ours informed me of this, even though he's never confirmed it himself. The same mutual friends, however, assure me that they don't think he'll cheat on me. I'm torn. On the one hand, I want to trust my friends’ judgment, and I really like this guy. On the other, I'll feel like a fool if I ignore the conventional wisdom and get burned. I'm all for communication, but I'm afraid to broach the subject with him, because if I imply that I think he might cheat on me then that might destroy any resolve that he had not to cheat. The question is, can people change?--Cautiously Optimistic

  • Quick 'n' dirty sex advice, summer edition

    June 27, 2013

    Happy summer, hot stuffs! It’s that time again, time for beer gardens, tankinis and another round of quick ‘n’ dirty sex advice, because though the days may be long, our attention spans are short. Let’s hit it and quit it (but not before sharing it with all your friends please. I work very hard!).

  • Help, I'm no longer attracted to my partner!

    June 12, 2013

    I have been in a monogamous relationship for three years now. Our sex life has always been fun and adventurous. We have tried almost anything we could think of, Google or read about! For the last couple of months, I have felt a loss of sexual attraction to my partner. There is no doubt I love him and do not want to be with anyone else at this time, and he says he does not want to bother finding someone else either, but I do not know how to tell him I am not sexually attracted to him anymore. It is becoming a problem because he still has a ton of sexual energy left for our relationship and questions of infidelity are coming up. I do not know how much longer, "I'm really tired right now" or "I am not really in the mood" will last. I am lost at approaching this situation.--Show Me Something New

  • Advice: Am I leading my friend on?

    June 5, 2013

    My friend with benefits told me he has feelings for me and wants to date me. I told him I hadn't thought of him that way and to let me think about it. We continued to be physical for a while, but I came to the decision that I don't want to date. I told him that and we've stopped being physical, but still talk every day. I've told him I'm afraid I'm leading him on and he told me he knows where I stand. He's also told me he still feels the same way and will continue to try. In an ideal world, I wish I could have him as my friend with benefits, but I know that's out of the question. I know I am leading him on, so my question is, what is the right thing to do? I love talking to him all the time and don't want to lose him as my friend. Do I need to give him space though?--What Now?

  • The case of the disappearing boyfriend

    May 22, 2013

    I was with my boyfriend for about seven months. Everything was fantastic, as far as I knew, until one day he just decided to disappear. No, really, I mean disappear. I couldn't get in touch with him via text, phone calls, anything. One night we were on the phone saying "goodnight" and "I love you," and the next day he was completely gone. I've racked my brain trying to figure out what went wrong, but I can't figure it out. It's been over two months now, and I've stopped trying to get ahold of him, but I'm having a really hard time moving on with no explanation, no answers, no closure ... Any advice?--Disappearing Boyfriend

  • Advice: I cheated a year ago. Should I come clean now?

    May 8, 2013

    I cheated on my boyfriend a year ago. We broke up for other reasons, but I still feel a lingering sense of guilt about what I did. Should I tell him about it or let it go? We talk and stuff, but I wouldn’t say we’re friends now exactly.--Too Little Too Late

  • Advice: Can a non-Jew join a Jewish dating site?

    May 2, 2013

    I've spent the last year-and-half dating dudes from OKCupid, but now I'm in a place where I'm looking for a more serious relationship. I've been looking for alternatives to OKC, as well as meeting dudes IRL (in real life), and I've been thinking that JDate would be a good match for me. I was raised Catholic, and my family still celebrates Christmas and Easter, but I find that I have the best relationships with Jewish guys. What's the etiquette for joining a site like this when I'm not actually Jewish? --Goy Seeks Boy

  • 'Gay accents' and when it's OK to butt into a couple's life

    April 11, 2013

    Hey Anna, your article responding to gay marriage/the idea of marriage made me decide to ask you this. Also, the Macklemore song ... I may be just being stereotypical but I don't know what to do. What do I do if I think my sister's fiance is gay? I am totally for gay people. Love them. Though I do not have a very good gaydar unless they are extremely flamboyant. I honestly probably won't do anything. I can't tell her what I think or I feel like it would get awkward between us. He is from the South, and it might be his southern accent, but I also sense the stereotypical "gay" voice in his. Where does that voice even come from? All gay guys don't have it. Sincerely, A Fellow Palindrome

  • Advice: Can I support gay marriage but not marriage in general?

    March 27, 2013

    Is it possible to support same-sex marriage at the same time that I don't support marriage in general? I respect and love my gay friends and certainly wouldn't want to deny them any of their rights, but I've never believed in marriage as an institution, and I find myself at odds. --Confused but Hopeful

  • Quick 'n' dirty sex advice: spring edition

    March 21, 2013

    Welcome to spring! It’ll still be cold for two more months, but that doesn’t mean we can’t dream about putting our ski masks away and of summer hookups to come. With a new season comes a new quick ‘n’ dirty column, advice for the short of attention but long of time-wastiness.

  • How much should bisexuals disclose on dates?

    February 20, 2013

    I’m a bi male who mostly has experience dating women, but after my last breakup am into exploring my options more with men. I’ve been on a few OkCupid dates with guys but don’t have a ton of experience. How much do I need to disclose to potential guy dates about my sexuality?--Can’t Bi Me Love

  • Advice: Throw the dating rules out

    February 6, 2013

    I like this guy and we see each other around a lot and talk sometimes but should I be all old-fashioned and wait around for him or grow some and ask him?--Waiting

  • How do I deal with separation anxiety?

    January 17, 2013

    I have developed separation anxiety for the first time in my life. In the 10 years I've been dating I've never been one to be overly attached to my mate. I mean I'm full of affection and miss my beloveds when we're apart but this time it's different. My man was recently away for seven days, and unreachable by phone, and in that time, when I wasn't fervently finding things to try to distract myself from the empty feeling he left me behind with, I was literally staring at the phone wishing it would ring. I'm a little worried for myself. I don't want to find myself creating a secret closet shrine if he's ever out of touch again in the future. Got any advice that'll keep me from turning into a bad '50s love song?--My Boyfriend's Back

  • Can my girlfriend get pregnant from anal sex?

    January 17, 2013

    I had sex with my girlfriend in her ass, and sperm out in her ass, so is there any chance of pregnancy. Please inform urgently. --Scared

  • Quick 'n' dirty sex advice: winter edition

    December 19, 2012

    It's winter (almost)! (Also, gross). That means it's time for another quick 'n' dirty-style advice column. Grab some mulled wine and come sit on my knee. If you missed the fall quickies, read 'em at your leisure. It is winter, after all, what else are you doing?

  • Should I cheat on my fiance?

    December 15, 2012

    I am confused. I am engaged to a beautiful woman and we are set to have a destination wedding this upcoming spring. We have been through thick and thin together and have stuck by each other's side for the past 7 years. About 2 weeks ago, I met a woman at a bar and the attraction and chemistry was immediate. We ended up kissing that night and we have kept in touch everyday through texts and phone calls, most of them very explicit. We want to have sex together even though she knows about my fiancé and she swears we would only do it to overcome our extreme physical attraction to each other.

  • Advice: Help me stop overthinking during sex

    November 21, 2012

    I've been out of the sex game for a while, save for a very casual relationship that happens sporadically. However, I met a girl recently and sex is imminent. I'm excited about it but worried because I'm having a hard time letting people touch me, just relaxing and enjoying sensation. My last relationship was largely sexless and took a serious toll on my ego, and now the little sex I have had in recent months is fraught with anxiety and over-thinking, and I don't want that to happen this time. How can I get back into my body?--Fraught

  • Advice: Dating a 36-year-old virgin? Dump him!

    November 7, 2012

    I started dating a guy about a month ago. I really like him and am interested in seeing where it goes, except for one thing: He's a 36-year-old virgin who's waiting until marriage to have sex. I've been sexually active for well over a decade, and I feel like this is too big of a difference to overcome. Plus, if we do become serious, I'm not willing to wait until marriage to find out if we're sexually compatible. Do I dump him or give it some time? Or try to convince him that waiting isn't necessarily the best idea?

  • I'm in love with my best friend who's taken. Do I tell him?

    October 24, 2012

    Over the last month I've fallen in love with one of my best guy friends. Usually I would tell him, but the problem is he has a girlfriend. Trust me when I say I am trying not to be some home-wrecker, but it's becoming more and more difficult to hide my real feelings. Do I tell the guy I love how I feel or continue to love from afar?

  • Advice: I'm liberal with a Republican fetish. Is that creepy?

    October 17, 2012

    I am afflicted with a persistent sexual fantasy that I'd rather not have. In recent years, I have developed a slightly unhinged attraction to Republicans. I'm your typical college-educated, urban-elitist lefty. I want saved whales, married gays and socialized everything. But when a cute girl tells me that Ronald Reagan is her personal savior, I am sent into a sexual frenzy. I feel it important to clarify what this bizarre fetish is not; it is not "hate [bleep]ing," nor is it one of those opposite-attracts, tension-filled things. It's much more of a role-playing thing, because in the fantasy I am right-wing too. I have sought out such women online, and I have behaved unethically by lying to them, but it really doesn't work without the lying.

  • Advice: 'My ex is stealing my friends!'

    October 3, 2012

    My ex is stealing my friends! Two months ago I broke up with my boyfriend; let's call him "Sam." We had a lovely, loving relationship, but I ultimately didn't see it going anywhere. So after much deliberation and heartache, I broke it off. We met through a longtime mutual friend; let's call him "Frank." Frank is my ex's best friend and my best guy friend. Now Frank is guilt-tripping me about the breakup, telling me I'm no longer on his "nice list" and generally acting like I'm a bad guy. This is in jest, but also not. It feels a little "bros before hos." I also found out that I'm not invited to another mutual friend-of-my-ex's wedding, which I was previously told I would be invited to. My best guess is that it's because of the breakup. How do I maintain these mutual friendships post-breakup? How do I feel less crappy about it all? Is it fair that I'm feeling a little mad at my ex for stealing these friends?

  • How do you dispose of unwanted sex toys?

    September 26, 2012

    I'm wondering how to properly dispose of unwanted sex toys. Years and years ago when I started trying out different kinds of toys, I bought several items that I've since discovered don't do anything for me. I'd just chuck them in the trash but the vibrating ones come with electronic parts and from what I understand, it's horrible for the environment to just throw away electronics. On the other hand, I don't suppose the local recycled computer parts garage is going to want them either. Any advice? Is our sex-positive culture just doomed to hurt Mother Earth?

  • Quick 'n' dirty sex advice, fall edition

    September 19, 2012

    It's fall! That means it's time for another quick 'n' dirty style advice column. Oh yeah. If you missed the last one, read the summer quickies here.

  • Advice: Time to dump that on-again, off-again relationship

    September 13, 2012

    I am currently in a debate with my head and my heart on if I should rekindle my relationship with a recent ex. My heart says "Yes, go for it! He's amazing, wonderful, funny, sexy, smart, and your best friend!" Yet my head (and everyone including key family members around me) says "Hell no, what are you, nuts?!" We dated on and off for two years and have been off now for 5 months. I moved out, got promoted and have a great life going on. He has a house, a career and we always have the best time together. I just don't want to hurt everyone around me for making a decision to be with him. But what I don't understand is why everyone has an opinion on it in the first place. It seems like these people are so unsupportive of my choices and see something in him that I don't? They never dated him, I did. It's so overwhelming to explain to them I don't want to bother, but this is the love of my life. I'm lost and confused. Any advice?

  • Advice: Is dating a younger man a bad idea?

    September 5, 2012

    I'm 28 and a young man of 21 has been showing interest in me. I have known him for many years because he lives two blocks away and his parents are friends with mine. I also have a 19-year-old brother who looks up to him. I have been getting to know him, but we have yet to go on a date. I'm nervous about it. I am attracted to him and would like to give him a chance, but sometimes I think this could backfire. He is very focused on school and he works full-time, and from what I know is a really good person. He has always been very mature for his age, which is why I am even considering giving him a chance. He plans on working full-time after graduation and even said he would, "take care of me." He said he was tired of the way younger women act. I'm not sure if I should pursue this! I do have a friend who is 30 and engaged to a 23-year-old, so I'm thinking there may be some hope! Any good advice?

  • Advice: OK to pursue a guy if he's 'seeing someone'?

    August 29, 2012

    There is a guy I'm interested in, and I want to get to know him better. We have had a few conversations about basic business or networking. A friend of mine recently had a conversation with him and he shared with her that he is "seeing someone" and broke it down to say to her, "He's investigating that possibility still and is willing to go there if his investigation yields promising results" in regards to the girl he's seeing. My question is, would it be wrong or leading myself astray if I still attempted to get to know him and possibly pursue something romantic? I don't know him as well as my friend, so we have not had any personal or romantic discussions. I just know he seems like a great guy, attractive and has great values, and I really wanna see if I can take it there. I'm just wondering if I'm wasting my time since he is "seeing someone."

  • Advice: Guys don't want to date me. Am I too nice?

    August 22, 2012

    I'm 26, single and, save for an amazingly brief relationship when I was 19, have been single all of my life. I seem to have no trouble making friends, male or female, and I am known to be a very personable, intelligent person. But somehow these qualities don't seem to translate in the dating world. I've had plenty of male friends say "the guy who gets you is really lucky." But all I can think is, "But that's not you?" The guys I've had crushes on have somehow morphed into friends who ask me for advice. So evidence suggests I'm a good person, but am I just not attractive enough to date? Was there a flirting/signals class I slept through, but caught Nice Girls 101?

  • Advice: 5 sex toy tips for beginners

    August 15, 2012

    My boyfriend and I want to incorporate sex toys into our lives but we're both newbies. It seems a little embarrassing to walk into a store, especially because we don't know exactly what we're looking for. Do you have suggestions?

  • My girlfriend won't come out to her parents...again

    August 8, 2012

    I'm a lesbian who's been in a committed relationship with the same woman for four years. We've recently been talking about marriage and starting a family. My one concern—she hasn't told her family about our relationship. She came out to her parents a decade ago, but they've never really accepted it. I think they're convinced she'll "end up straight" and marry a man. Basically they're in denial. But I don't think that means she shouldn't confront them and be honest about being in a long-term relationship. Any suggestions on how to deal with this?

  • Advice: Is being too tall a turn-off?

    August 2, 2012

    I'm tall—maybe 6-feet, 2-inches—but regardless it is noticeable when I fly. So, this can affect who looks at me to date in reality. What do you think is too short for me to pursue because women get caught up in the appearance of a couple, whether they "look right" or not?

  • Top 5 Olympic sports that could also be sex positions

    July 26, 2012

    We've always appreciated that "Naked Gun" joke, where Leslie Nielsen says he likes his sex like he likes his basketball: "One-on-one and with as little dribbling as possible." With the 2012 Summer Olympics kicking off Friday, this got us thinking about the undeniable allure and power of the physical body in top form. Despite the Olympic Village mayor Sir Charles Allen's recent remarksthat winning is more important than sex, we at RedEye happen to believe that the real feat of stunning humanity is not, in fact, shot putting or judo, but gettin' it on. With this in mind, we've come up with the top five Olympic sports that could also be sex positions.

  • Advice: What's the big deal with older women dating younger men?

    July 19, 2012

    Why do people judge when a younger guy wants to date an older woman?

  • Advice: How to deal with a broke boyfriend

    June 27, 2012

    I've been dating this guy for about a month. He's super awesome, super sweet, lots of fun, and a pretty good match for my personality. There's just this one little thing that has been causing me great anxiety. He's got no money and doesn't seem at all ambitious or willing to take risks with his career as an artist/musician. Don't get me wrong, I totally don't care about money. I don't judge, or want to be some rich man's quiet wife. What I'm concerned about is that in the short time that we've been dating, I've paid for nearly everything. And it's not like we're living large, either. He stays at my house about three nights a week, and so I cook him dinner/feed him breakfast. When we go out, I often pay for movies, snacks, public transportation, or a drink—they're all pretty modest things, but it's definitely adding up, and I'm living on a student-debt budget.

  • RedEye's mailbag: Quick 'n' dirty sex and love questions answered

    June 20, 2012

    It's summer, and because it's hookup season, let's do this week's advice column hookup-style, i.e. quick 'n' dirty? Yeah, you like it.

  • Advice: Do wedding dates freak guys out?

    June 15, 2012

    How long do you have to be dating someone before you can invite them to be your plus-one at a wedding? I've been on half-a-dozen dates with a guy, but we've known each other for over a year. I have three weddings this summer, and don't want to go solo, since most of my friends are in relationships. But, I also don't want this guy to think I'm getting too serious, too quick. I'm into him, but I'm definitely not ready to walk down the aisle with him or anything. Do wedding dates freak guys out?

  • Advice: Is it creepy to message my crush on Facebook?

    June 6, 2012

    I have met this girl a couple times and I find her to be very cute. The last time I ran into the girl, I got tongue-tied and didn't want to make myself look dumb. Now I was thinking that I could go and search for her on Facebook and see if I can do introduce myself that way. What do you think? Or should I go about it in another way?

  • Advice: Is my lack of experience at 30 a turn-off?

    May 30, 2012

    I'm almost 30 and have never been in a relationship. I blame this on a number of circumstances, but let's be honest. At this point, half the problem is that I'm almost 30 and have never been in a relationship. Even if I think someone is attractive, mentally or physically, I can't seem to convey that I'm interested without saying something along the lines of "Me Jane, you cute." To make it even more fun, I'm active online the most, and while I seem to have flirting down there, finding people who aren't states away to flirt with in the real world is a gigantic hurdle. While I'm not opposed to online relationships or even long distance, I'd rather meet people in person before I invest time and emotion in a deeper connection with them. Any suggestions for portraying availability and interest without giving away my complete and utter lack of experience with the opposite sex and keeping it local?

  • Advice: How to tell men dirty hands aren't sexy in the bedroom

    May 23, 2012

    I love men, and I gravitate toward dirty ones. Not dirty like kinky; dirty like rough and tumble, scruffy-faced and dirty hands. I also really enjoy those hands in special, delicate ecosystems of mine, if you get my drift. This has resulted in some issues, such as a lovely jalapeno burn down under from a guy who made me nachos one night and didn't wash after. I need a nice, sexy way to tell my men, "Wash your freaking hands before you go spelunking!" Advice?

  • The best summer hookup spots in Chicago

    May 16, 2012

    My favorite hookup season is right around the corner! Can you tell me where are the best places to meet people in the summer in Chicago?

  • Advice: Is it OK for straight guys to hit on lesbians online?

    May 9, 2012

    My question is about online dating. I'm a straight male who finds himself way more attracted to bi or gay females than straight women. This applies to sexual attraction, but even more so with emotional attraction. Speaking in blanket terms, straight women sometimes seem too prudish or conservative for my liking. And there's just something extremely attractive about a strong, self-sufficient, maybe tomboyish, gay female that really does it for me. So on to my question. Is it wrong for me to message females on OkCupid that have their orientation set to gay if my intentions are romantic? I don't want to be disrespectful or out of line, but I tend to be way more into the gay female profiles on OkCupid compared to the straight ones. And wasn't there some recent studies that came out proving that female sexuality is more fluid than male sexuality? Thanks for your help!

  • Advice: Help! I'm 32, single and freaking out

    May 2, 2012

    I'm 32, single and haven't dated anyone seriously in the last decade and have only dated a few guys casually in that time. At my age, most of my friends are married and are now starting to have kids. I'm freaking out a bit. I want to get married and have a family, and I feel like time is running out. I haven't tried online dating because I really don't think it's for me, but at this point, I don't know what else to do. Any advice for meeting marriage-material men at this age?

  • Advice: Is a relationship doomed when the woman earns more than the man?

    April 25, 2012

    I make considerably more money than my boyfriend. He makes a decent living too, but hasn't been nearly as ambitious in his career as I have been and has talked about wanting a new job for years. He says it doesn't bother him that I make more, but I think it does. I know he wouldn't want his friends to know and he still insists on paying for things. How can I make him feel better about this? And, sometimes I do judge him, not because he makes less money than me but that he hasn't tried to go farther in his career. I've tried to encourage him to look for a new job and have offered to help with his resume, but he just keeps avoiding it. How do I make sure this doesn't drive us apart?

  • Sex starved and looking for love

    April 19, 2012

    I read your article, "Don't Date Your Roommate." I wish I could have a female roommate. I haven't had sex in the last seven months. I feel very horny. I am a 30-year-old African living on the North Side. I am very much interested in dating white ladies. What do you advise me?

  • Why is sex at 30 so awesome?

    April 11, 2012

    I had heard from older friends that sex for women gets better in their late-20s and 30s, but I never really believed it until I hit 30. Holy crap, it's true! My sex drive is way more intense and I have more orgasms more easily than ever before. Not that I need justification to enjoy my awesome new sex life, but I'm just curious, why does this happen?

  • Is dating your roommate a bad idea?

    April 4, 2012

    I just started seeing this really fantastic girl. She's fun, smart, ambitious. It's too soon for us to be really serious, but I do like her a lot. Just one problem: She's my roommate. We're both 21, live in a house with three other people, and there's a strict 'no couples' rule when we seek roommates. Like I said, we really like each other but it's only been a few weeks, and I don't think either one of us is up for making life changes for the relationship at this point, but we both want to see where it goes. What do we do?

  • How do I deal with my boyfriend's depression?

    March 29, 2012

    Dear Anna,

  • The key to talking dirty during sex

    March 21, 2012

    My boyfriend and I are having sex. It's great sex. But lately he has wanted me to beg before he enters me. I don't know what to say. I try and try to come up with something he'd like. I beg by saying "master" but he doesn't want me to use master. He said it's a turn off. What should I say?

  • Advice for men who suck at picking women up at bars

    March 15, 2012

    I'm terrible at talking to women in bars. I always feel so awkward, and never know what to say. On the rare occasion that I've gotten a few numbers from girls, it never leads anywhere. What can I do to get over myself?

  • I'm in love with a 40-year-old virgin

    March 7, 2012

    I have recently met a woman I am falling madly in love with. As a divorced guy at the age of forty I never thought I would say that again. I have dated, a lot, and I just figured love was something that didn't exist for me. We do everything together, hike, yoga, climb, play silly games of Scrabble way too late and then fall exhausted into bed together, where we do nothing.

  • Male grooming 101: Is body hair a turnoff?

    February 29, 2012

    I was having lunch with some lady friends the other day and the topic of hair came up. They were discussing eyebrow threading, bikini waxes, etc., and it got me thinking. How important is male grooming? Besides tidying up the downstairs area, how big a turn-off are things like nose, ear, eyebrow, back hair?

  • Why it's absolutely OK to date 2 people at once

    February 15, 2012

    I started casually dating a guy about two months ago. We've been on half a dozen dates, and I like him. We're very sexually compatible (haven't slept together yet but have done everything but), but I'm still not 100 percent sure if there's anything long-term in our future. Last week, a friend of a friend and I hooked up at a party, and now he's asking me out on a date, and I'd like to go out with him to find out if we're compatible. So now I find myself dating and hooking up with two men simultaneously. This is the first time I've done this, and I feel like it's a bit awkward. Is it totally OK to do this? Do I need to tell the guy I've been seeing longer about this new man? How do I handle this without it winding up like a really awful romantic comedy where I book two dates on one night?

  • A wife's denial leaves a husband hopeless

    February 8, 2012

    I am very depressed and confused. I have been married 16 years. My wife has cheated on me several times in the past. She was laid off work for two years ago and started hanging at the local loser bar just about every day. This made me very upset. She told me it is to get "out of the house" and to socialize. She promised me nothing was going on. She was pretty much drunk almost every day. Six months ago, I got an anonymous letter in the mail saying, "Your wife isn't who you think she is." Again she said nothing is going on. I recently went to her watering hole and some barfly and a bunch of dudes were on the other side of the bar. I overheard the woman tell the dudes that she wanted to introduce them to my wife. One of the dudes said, "Oh, she's the woman I heard so much about. I heard a lot about her. A lot!" Again she said nothing is going on. What am I supposed to think and do? She denies anything remotely is going on.

  • 3 steps to feeling sexy, confident in the bedroom and beyond

    February 1, 2012

    I used to have no problem with feeling sexy and comfortable in my body and with my sexuality. But after a recent weight gain, I started to be self-conscious and unable to get into the "Sexy and I Know It" mindset. I lost the weight, and I still can't seem to get back my confidence. My husband will compliment me, but I'll still find something wrong. I'm 24, so I don't know if this is just a phase. The only method that seems to get me in that uninhibited mindset is to have a drink. How do I tap into my dirty side and let out my inner bad girl freak without feeling uncomfortable/stupid?

  • How do I confront my boyfriend about finding child porn?

    January 25, 2012

    I live with my boyfriend of nearly five years, and we have a pretty good relationship. Not long ago I came across a picture CD that was with some items of his that had been in storage. The CD was titled "pixxx." Curiosity got the better of me and I put it in the computer. However, I was horrified to find that they are photos of very young girls, children, in their underwear and in sexual poses. They appear to have been from various sources and likely downloaded from the Internet. According to the file creation dates, they were burned to the CD about six years ago. My question to you is: Do I confront him and see what he says, or do I just bring it straight to the police? Do I turn him in or do I drop it off anonymously? I am torn because I am having a hard time accepting it is his CD. I didn't think the man I love could be that way. Maybe it could have been an old roommate's CD? This is horrible and devastating, and I need a little advice. Thank you.

  • STDs and sex: What you're obligated to disclose

    January 18, 2012

    This super dominant dude has been all into me the last couple days. He has a primary partner/girlfriend, and has been chatting me up/calling me/texting me. So we get down to the STD conversation, and turns out he won't play with me, not because I have herpes, but because one of my regular partners does. Is this normal? Was I even obligated to discuss that? Should I have even mentioned it? I mean, in a way, I was sharing someone else's secret. I'm totally unsure of my ethical obligations in this case. Do I have to tell everyone I might potentially have sex with that one of my regular partners has it?

  • Wise to share bedroom desires on your online dating profile?

    January 11, 2012

    I broke up with my long-term boyfriend recently, and am thinking about re-activating my OkCupid account soon. One thing I discovered in my last relationship is that I'm interested in exploring kinkier sex, as long as it's with someone I trust. My question is: How can I convey this on my profile? I feel like if I say it outright, I might attract a lot more skeezy guys or get explicit messages that I don't want. Should I mention it at all, or save the kink talk for when I meet men in person?

  • How to talk pubic hair with your girlfriend without getting smacked

    January 4, 2012

    I adore my girlfriend. She's hot and smart and funny—the whole package. She also happens to be very petite, with a youngish face, which is all well and good, except when combined with the fact that she waxes her hoo-ha, it makes her look, well, pre-pubescent. I know it's her body, but I'm the one that's down there all the time, and frankly, it weirds me out! How can I broach this subject without getting smacked?

  • It's almost NYE: Time to dump your seasonal boyfriend?

    December 28, 2011

    I've been dating a guy for about a month now. We're not that compatible, and to be honest, I was mostly spending time with him to avoid the inevitable holiday loneliness. This sounds worse than it is. Who knows, maybe he's doing the same thing? So, my question is two-fold. One, since NYE is coming up, am I obligated to spend the evening with him? And two, how do you break up with someone you were only seasonally dating without making it obvious that's what you were doing?

  • How to get over an inappropriate crush

    December 14, 2011

    If you like a girl who's dating a good friend of yours, what do you do? They started dating about two months ago and I couldn't say anything because of my bro-code obligation. And now, I like her even more and I can't just forget about her or stop liking her since she is a permanent member of the social circle. I can't claim my feelings because she is head over heels for this guy and I doubt I have a chance. Not to mention it would make every interaction with her awkward. What would be the best option in this dilemma?

  • I'm bi, my girlfriend's bi-curious. How do I support her exploration?

    December 8, 2011

    I've recently come out as a bi man. Luckily, I've found an amazing "bi curious" girlfriend who's understanding. We have great sex. The relationship is developing nicely. One problem though, curiously, is her bi curiosity. To feel comfortable committing to the relationship, she needs the option to explore girls. Which I've granted. Encouraged even. But paradoxically, my openness causes her insecurity. She's from a more traditional part of the country, and by not wanting her to be exclusive, I'm not fitting into the traditional role of committed boyfriend. There's also just fear of the unknown. Will she like girls better? We've been really good about talking this out, and have talked a little about bringing another girl to bed, but is that really the solution? As a decorated threesome veteran, does this sound like a road to bliss or a potential purple heart? Are there other, less cliche ways to support her exploration?

  • If you have an affair with a married man, be prepared to hear from his wife

    November 28, 2011

    So, I had a tryst with a married man. I thought better of it eventually and ended it, but his wife still found out. And recently, she wrote me an email. I don't know his wife at all. What is my responsibility here? Do I write her back? Should I stay the f**k out of it (even though clearly I'm already involved)?

  • Do I tell my friend I'm dating her ex?

    November 23, 2011

    I've been seeing one of my friend's exes. She was a very close friend years ago, but our relationship has dwindled. They were broken up for two years before we got together, but my friend was totally in love with him when they were dating, he broke her heart, and it took her a very long time to get over him, even when she has had other boyfriends, she was still hung up on him.

  • 'I want to dump my girlfriend because she's poor'

    November 10, 2011

    I rarely get into relationships, however, one night I met a girl and we instantly became girlfriends. Now I've been trying to backtrack and play the "getting to know you game." She mentioned she was in debt, which was initially a complete turn off seeing as how I love money and despise all people with poor spending habits. And when I questioned her about why she was in debt, she got very defensive and basically said it was none of my business. I think it is my business, especially if she has some sort of gambling or drug problem she hides. Am I being rational for wanting to know and setting myself up for future success and avoiding pain down the road? Or are there really just some things that are "off-limits" conversations. I want to dump her because she is "poor." I know that sounds awful but it's the truth, and I don't want to play the mommy in the relationship. I am 21 and she is 29. I figured an older woman would have their stuff together more than someone my age.

  • Queer & confused: 'I find myself wondering if I'm somehow straight after all'

    October 27, 2011

    I'm 29 years old, and I've been out and totally happy living as a queer person since I was about 21. I had only dated queer women since I came out, although I knew I was open to other possibilities. My sex life is pretty polyamorously perverse, and I tend to connect with people on a lot of levels besides gender and physical sex, so you know, whatever. But still, last year I surprised no one more than myself when I ended up in a fairly lengthy relationship with a boy—a sort of queer boy, to be sure, but a boy nonetheless. I felt incredibly awkward because no matter how non-traditional, non-straight our relationship was on the inside, it automatically got read as totally straight by the outside world. Throw into the mix that my physical appearance has gotten to be what would be termed sort of femmey over the years, and all of a sudden I was feeling really invisible as a queer person.

  • What do men get out of a guy-guy-girl threesome?

    October 13, 2011

    A straight guy friend of mine recently expressed interest in a guy-guy-girl threesome. I've always been perplexed this. What do the guys get out of it?

  • Getting dumped: How to cope

    October 10, 2011

    I'm trying to get over my ex-girlfriend who cheated on and dumped me. I've done so by cutting her out of my life completely, defriending her on Facebook, the whole shebang. But I still think about her constantly. And I've taken to writing her letters, but not sending them, as a way to cope with the urges I have to contact her. Is it helpful to have an outlet or am I just reinforcing my obsession with her?

  • How to ask for more foreplay in bed

    September 21, 2011

    I'm 21 with a 26-year-old boyfriend. I'm getting frustrated because whenever I want sex, he either blows me off and promises we'll do it later, or f**ks me so fast I barely have time to say "a little to the left" before he's done, and I'm wondering what I did wrong. I just want a little foreplay. Is that too much to ask?

  • How to make sober sex as hot as drunk sex

    September 8, 2011

    Contrary to popular practice, my boyfriend is significantly more interesting in bed when he's drunk-ish than when he's not. He's less passive, a little rougher, and more, like, SEXY. How do I tell him to f**k me like he's drunk?

  • Want to be more dominant in bed? Here's how

    August 30, 2011

    So here's the thing. My boyfriend is very dominant in the bedroom. I love this about him. He knows exactly what to do, what feels good to me, always takes control and is very manly. He has great intuition in the bedroom, always switching it up, making sure we are both having a good time and achieving the best climaxes possible. He's down for sex games, pretty much anything kinky he will do. I really do like this as well and I want to get more involved with it.

  • What to do when your partner doesn't want to have sex

    August 20, 2011

    My boyfriend and I have been dating for nearly 4 years. For about the last year and a half we have had little to no sex. I used to try to initiate sex with him, but was always turned down. When I turned to friends for advice everyone had the same answer: he is either cheating on me or he is gay. I know for a fact that he is not cheating on me. We have also had an in depth conversation about his sexuality. I have asked him over and over to seek out therapy or get some kind of help so that our relationship can thrive sexually, but he has yet to do so. I have tried everything, but nothing appears to work. What should my next move be?



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