I love my boyfriend but I fear we aren't compatible for the long term. How to know if it these are things that are important enough to justify breaking up sooner rather than later... [more inside]
posted on Jul 23, 2008 - 37 answers

Am I just happier being single? [more inside]
posted on Jul 22, 2008 - 30 answers

Am I fair in blaming a snail's-pace relationship on my weak ability to show affection? [more inside]
posted on Jul 15, 2008 - 24 answers

How does a very good man meet a very good woman? [more inside]
posted on Jun 24, 2008 - 29 answers

GirlfriendFilter: What should my almost-but-not-quite girlfriend of two months and I do to celebrate her birthday? [more inside]
posted on Jun 22, 2008 - 5 answers

I know a great deal about how romantic relationships develop with insecure people, but very little about what happens when the participants are already comfortable in their own shoes. [more inside]
posted on Jun 18, 2008 - 13 answers

I live in DC, and I'm in my late twenties. What I've found, at a time in my life when I'm really looking for something serious - all I can find is ass. [more inside]
posted on Jun 12, 2008 - 21 answers

Help me Don Juan Kenobi, you're my only hope; or How do you stay flirtatious, witty, and mysterious when you REALLY like someone? [more inside]
posted on Jun 4, 2008 - 11 answers

Don't be desperate. Okay, how? [more inside]
posted on Jun 4, 2008 - 22 answers

I'm 29, male, and with no significant relationship experience. I've been dating the same girl for a few months now and I'm still not sure, although she seems to be. How do I tell whether a relationship is worth sticking with? [more inside]
posted on May 16, 2008 - 24 answers

How do I develop a thick enough skin to date? [more inside]
posted on May 13, 2008 - 28 answers

The type of guy I like to spend time with isn't the type I like to have sex with. What now? Probably NSFW! [more inside]
posted on May 5, 2008 - 31 answers

How best do I meet with a girl from facebook? [more inside]
posted on Apr 16, 2008 - 10 answers

I have a bit of a dilemma. I dated this guy last year, and he introduced me to a friend in order to get him hired at my company. Flash forward to now, and he's finally been hired, and a referral bonus is coming my way. More deets inside, natch. [more inside]
posted on Apr 15, 2008 - 69 answers

BreakupFilter: How do I let someone down easy? How would you prefer to be told that someone just isn't that into you? [more inside]
posted on Apr 14, 2008 - 27 answers

Do I stay or do I go? A former flame wants to be a friend, and I'm honestly at wit's end about what to do. [long explanation] [more inside]
posted on Apr 13, 2008 - 26 answers

Is timing really so important in dating and relationships? [more inside]
posted on Apr 11, 2008 - 25 answers

I'm attracted to one of my university instructors (and we're approximately the same age, in case it matters). Is there an appropriate way to ask her out? [more inside]
posted on Apr 6, 2008 - 31 answers

What is the "normal" waiting time before asking for a second date? [more inside]
posted on Apr 5, 2008 - 26 answers

After ending things with a girl a few months ago, I've come to my senses and want another chance. Should I try and how? [more inside]
posted on Apr 4, 2008 - 30 answers

Relationship filter: So I am a freshmen in college and I really want to ask this girl out on a date, but I think there could be some issues with our lifestyles. She is a party all night long sleep all day kinda person and I am a more party for a while with friends then go relax at home. more inside. [more inside]
posted on Apr 3, 2008 - 20 answers

How can I be more relaxed, and less anxious (read: totally flipping out) about dating people I like? [more inside]
posted on Apr 1, 2008 - 8 answers

Where do single male computer science/physics/engineering nerd-types hang out in Chicago? [more inside]
posted on Mar 29, 2008 - 11 answers

I am a 38-year-old man who has many good qualities (I hope so at least) but two drawbacks which understandably be dealbreakers for most women - I am impotent and I have a small penis (around 4 inches on the rare occasions it is erect), so even if my impotence got treated I am not sure I could satisfy a women. On the other hand, I have heard that it's possible to have satisfactory sex life with a 3 inch penis, but have no idea how that can be. So basically I am what would be a figure of ridicule for many other men, and not exactly a strong candidate to be a boyfriend for most women either. However I know some women while still heterosexual may not want a sexual partner e.g. they may be celibate for whatever reason. And there may even be women who will overlook a sex life without penetrative sex for the right person. I have just come out of a four-year relationship which had lots of affection and companionship but not strong feelings of passion and obviously no sex, but I eventually want another relationship again and believe I have a lot of love to give the right person. How can I find her? [more inside]
posted on Mar 23, 2008 - 38 answers

After a four-year relationship ended disastrously, early last year, I've developed an interest in someone. The problem? A reliable source describes this guy as a complete douchebag. Given that I was previously badly burned, do I go out with this guy whose reputation precedes him? [more inside]
posted on Mar 17, 2008 - 43 answers

So there's this girl. She is brilliant and wryly funny and beautiful and we are grad students together in a program that will shortly be ending. Explain to me in the simplest possible terms - as though I were an extraterrestrial anthropologist with an academic interest in, but little direct experience with, human interaction - how I can show her that I'm interested in being more than friends... [more inside]
posted on Mar 12, 2008 - 20 answers

After a complete transformation, I need to practice flirting, in New York. [more inside]
posted on Mar 9, 2008 - 22 answers

What are the social norms and/or taboos regarding a single 44 year old women approaching men who are slightly more than half her age? [more inside]
posted on Mar 4, 2008 - 13 answers

I'm a straight guy and I have several kinks which drive me wild in bed. I'd like to date a straight girl who has similar kinks which drive her wild in bed. But I don't want to get into fetish lifestyles or anything extreme (unfortunately kink owners tend to get polarized into one big group of "alternative people" who dress in rubber and go to subterranean bondage clubs every week) - I just want a regularish relationship with some special orders in the bedroom. How do I do this? [more inside]
posted on Mar 2, 2008 - 18 answers

Please suggest fun date outings in Manhattan for a transplant and a New York City native. [more inside]
posted on Feb 29, 2008 - 2 answers

I've lost my religion and now I am going to lose my v-card, please help. [more inside]
posted on Feb 11, 2008 - 41 answers

Widow in her mid-thirties would like some dating tips... [more inside]
posted on Feb 7, 2008 - 35 answers

How to send that first email in the world of online dating. [more inside]
posted on Jan 28, 2008 - 47 answers

My girlfriend and I have religious and cultural differences. How can our relationship work? [more inside]
posted on Jan 21, 2008 - 47 answers

I have a date tonight with someone I blew off a long time ago. [more inside]
posted on Jan 21, 2008 - 41 answers

What to do now? I'm a single, mid-thirties female, and I have a crush. Oh, wait. It's a lot more complicated than that. I'm sorry this is so long... [more inside]
posted on Jan 16, 2008 - 37 answers

25 year old girl that hasn't had anything past a 2nd date in 6 years, what is wrong (if anything) with me? [more inside]
posted on Dec 30, 2007 - 43 answers

I'm freshly sprung on a new cutie. How do I take it slow? [more inside]
posted on Dec 16, 2007 - 20 answers

SM question?? (very personal) [more inside]
posted on Dec 16, 2007 - 22 answers

My girlfriend is having second thoughts about what she wants out of life. This could lead to a change and possible end our relationship. I'm scared. [more inside]
posted on Dec 15, 2007 - 27 answers

My roommate is stalking my sister. [more inside]
posted on Dec 11, 2007 - 31 answers

Mental illness/dating filter: Four years ago, I broke up with a great guy (possibly the right guy, definitely the wrong time). We've had contact maybe three times since then. Two years ago, at age 38, I was diagnosed as bipolar. Now he wants to have dinner. How much does he need to know about my illness and how do I explain it? [more inside]
posted on Dec 8, 2007 - 20 answers

I don't infatuate easily, and am very slow-to-warm-up with regard to romantic interests. What's a gal like me to do in the world of speed dating? [more inside]
posted on Dec 6, 2007 - 8 answers

How do you get over someone you work with? [more inside]
posted on Dec 4, 2007 - 12 answers

How can I keep my head on straight as a first time "friend with benefits"? Is this just not for me? Of course there is a LONG story after the jump. Wee, come with me! [more inside]
posted on Nov 30, 2007 - 25 answers

I'm a 40-ish guy who just had his first date in a long time. It was with the woman who is Beatrice to my Dante, and I think the date went well. She said we could get together again in the future. What now? [more inside]
posted on Nov 27, 2007 - 30 answers

How to handle my boyfriend's father? [more inside]
posted on Nov 2, 2007 - 54 answers

Is there something wrong with my dating priorities, or is this totally normal? [more inside]
posted on Nov 1, 2007 - 27 answers

how do i actually date with internet dating? [more inside]
posted on Oct 30, 2007 - 24 answers

How confident should you be about a relationship at the start? [more inside]
posted on Oct 20, 2007 - 21 answers