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 - 20 answers

How do I set more reasonable expectations for relationships? [more inside]
posted on May 15, 2008 - 7 answers

How do I develop a thick enough skin to date? [more inside]
posted on May 13, 2008 - 27 answers

I'm living overseas and am interested in dating a guy that I've met here. The problem is that he lives in a community where the men have a reputation for loving and leaving foreign women - how do I know if he's different from the rest? [more inside]
posted on May 9, 2008 - 17 answers

Single mom/Single parent: How does one go about building a lasting relationship with a single mother, to show her that you will not only be there for her, but also for her son? (She's 22, and he's under five I'm assuming.) [more inside]
posted on May 5, 2008 - 10 answers

I need help coming up with a fabric based vacation in California. As in literally, fabric. The stuff you make socks and clothes out of. Is there such a thing? [more inside]
posted on May 5, 2008 - 17 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

QUICK! Should I ask this guy to a party tonight? [more inside]
posted on May 3, 2008 - 43 answers

What is an appropriate birthday gift to give to someone you've only just started dating? [more inside]
posted on Apr 26, 2008 - 28 answers

When do you ask the person you are dating if they are seeing anyone else, and how or when do you talk about or bring up the subject of being exclusive?
posted on Apr 25, 2008 - 13 answers

I've come to the realization that I'm head-over-heels crazy about a co-worker. [more inside]
posted on Apr 24, 2008 - 55 answers

I'm a student in the UK and have decided to take a job in the U.S. starting in the autumn. Is there any hope for me to be in a romantic relationship until then? [more inside]
posted on Apr 20, 2008 - 7 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

should i date other people? [more inside]
posted on Apr 11, 2008 - 22 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 to woo a French-American woman? [more inside]
posted on Apr 2, 2008 - 34 answers

How do I ask my friend on a date? [more inside]
posted on Apr 2, 2008 - 36 answers

Is non-stop chatter a necessity in the early stages of dating? [more inside]
posted on Apr 1, 2008 - 24 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

Kinda like the anonymous question a little bit ago, but looking for the geeky gay guys in Phoenix. [more inside]
posted on Mar 30, 2008 - 6 answers

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

Why do some women on dating sites post pictures of themselves with men as their primary photos? [more inside]
posted on Mar 28, 2008 - 21 answers

Question for divorced men who have since remarried, gotten into a serious relationship: how long after separating before you felt ready to date someone seriously. Not when DID you start dating or not, but when did you feel in your heart that you were ready to date. And was sealing custody/alimony deals a part of this, i.e. did you need this stuff nailed down before you felt ready to "start a new life." And did you feel like you needed a second adolescence after the divorce, whether that meant going wild, or just spending a lot of time doing whatever you wanted, without having to consider someone else's feelings/schedule.
posted on Mar 28, 2008 - 10 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

I'm on the cusp of dating someone soon after a breakup. Is it too soon? [more inside]
posted on Mar 20, 2008 - 23 answers

How proactive should a girl expect a guy to be about suggesting dates during the early stages of a relationship? [more inside]
posted on Mar 20, 2008 - 22 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

Psyche is a slippery slope. Advice on dating as a thirtysomething college student? [more inside]
posted on Mar 16, 2008 - 16 answers

What is the Best NYC Locations to Meet Singles? [more inside]
posted on Mar 16, 2008 - 5 answers

What are some necessary tips for approaching and meeting guys in gay bars, esp. when I'm alone? [more inside]
posted on Mar 15, 2008 - 6 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

How does a gay man go about dating women? [more inside]
posted on Mar 11, 2008 - 31 answers

Dating a divorced man. Help me rationalize this relationship mess before I gouge my eyeballs out. [more inside]
posted on Mar 9, 2008 - 76 answers

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

Does anyone have any tips for dating with a tight budget? [more inside]
posted on Mar 9, 2008 - 25 answers

What is the right dating etiquette after a good first date? [more inside]
posted on Mar 5, 2008 - 18 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 am a 26-year old straight male, and I do not seem to inspire attraction by women. While I am generally liked and appreciated as a friend, I am consistently told by women that they are not interested in me romantically. What can I do to change this? [more inside]
posted on Mar 3, 2008 - 51 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 keep attracting girls who are incompatible with me. How can I get women who I actually have a future with? [more inside]
posted on Feb 27, 2008 - 17 answers

BostonDatingFilter: Are the single men too scattered around? Where are they? [more inside]
posted on Feb 26, 2008 - 27 answers

Looking for dating ideas that meet three simple criteria: 1. Inexpensive. 2. In Boston/Camberville and T-accessible. 3. Doable in this weather. [more inside]
posted on Feb 25, 2008 - 18 answers