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?
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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!
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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?
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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?
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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?
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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?
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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?
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How do I deal with my boyfriend's depression?
March 29, 2012
Dear Anna,
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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?
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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?
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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.
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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?
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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?
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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.
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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?
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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.
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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?
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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?
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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?
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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?
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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?
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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?
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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)?
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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.
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'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.
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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.
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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?
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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?
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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?
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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?
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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.
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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?
