I asked someone over to review their art portfolio, but I also have designs on asking them out on a date. Tacky or just being creative? [more inside]
posted by zenpop on Dec 28, 2009 - 34 answers

Help me be more direct in telling someone I like them, but not so direct as to be weird. [more inside]
posted by anonymous on Dec 27, 2009 - 41 answers

What am I doing wrong? I am 25 and HAVE NEVER GONE ON A DATE. I have always been attracted to women only, and I am funny, intelligent, and reasonably good looking. I make friends easily, but I don't know how to ask people out, and I've only been asked out by weird guys [more inside]
posted by anonymous on Dec 27, 2009 - 17 answers

The New Year is approaching and I need some guidance on how to move forward with my life. [more inside]
posted by anonymous on Dec 26, 2009 - 13 answers

I'm a twenty year old gay woman. For 2010, I want to learn how to flirt with other women. [more inside]
posted by anonymous on Dec 24, 2009 - 13 answers

How do you deal with instant messaging early in a relationship? [more inside]
posted by anonymous on Dec 21, 2009 - 18 answers

Ice Skating in NYC. Recommendations please? [more inside]
posted by cazoo on Dec 17, 2009 - 10 answers

Question about casual dating and newfound attractiveness. [more inside]
posted by anonymous on Dec 16, 2009 - 14 answers

What do you wish you knew about Mainland Chinese dating and relationships that would have made your relationship easier? What are some common sources of misunderstanding between Westerners and people from China? [more inside]
posted by anonymous on Dec 15, 2009 - 2 answers

I've been in a long-distance relationship for five years, we'll call him "M." It is a damn challenge. During those five years, M and I have gone back and forth between an open relationship, not a relationship, and a long-distance relationship. We've both dated other people, but never gotten serious about anyone else. I just started dating someone, "J." Do I need to tell J about M? And should I even be dating other people? [more inside]
posted by ajarbaday on Dec 13, 2009 - 18 answers

I'm extremely infatuated with my boyfriend of 1 year, to the point where it's getting a little annoying. Advice? [more inside]
posted by anonymous on Dec 11, 2009 - 20 answers

When is the right time to discuss moving in together when you've recently translated your relationship from skyping for 3 years to actual dating in person for 2 months? [more inside]
posted by audio on Dec 10, 2009 - 30 answers

Help me brainstorm a way to ask out a girl. But wait! There are complications. [more inside]
posted by anonymous on Dec 10, 2009 - 25 answers

What's the protocol on calling and/or texting for a booty call with a friend you've recently hooked up with? [more inside]
posted by anonymous on Dec 9, 2009 - 16 answers

Help me overcome my fear of rejection - the catch - it's a fear of rejecting other people [more inside]
posted by Chrysalis on Dec 9, 2009 - 11 answers

I have been dating a variety of people, for various lengths of time, for about two years now, however I dont seem to like anyone in the special way which would allow me to enter into a full-fledge relationship with them. Is this normal or is this just a case of being too picky? [more inside]
posted by anonymous on Dec 9, 2009 - 8 answers

I had a first date on the weekend with someone I was matched with on an online dating site. We’ve been emailing each other for a couple of weeks and getting on really well – lots in common, similar outlook and aims in life. In person she ticks pretty much all the boxes too, physically and personality wise... except for her teeth. [more inside]
posted by infinitejones on Dec 6, 2009 - 29 answers

How do I tell my friend the truth in a way that she can hear it, then take what she can from it and do what feels right to her? [more inside]
posted by Hydrofiend on Nov 29, 2009 - 29 answers

Do I bear-up being alone for the next six months to a year, or...? [more inside]
posted by paulg on Nov 28, 2009 - 42 answers

How can a gimp who's got a lot going for himself get a date and maybe even get a little somethin' somethin' after a loooong dry spell? More details with minimum self-pity inside. [more inside]
posted by anonymous on Nov 27, 2009 - 13 answers

How does one ethically play the field? I need advice on dating and being intimate with more than one person. [more inside]
posted by anonymous on Nov 26, 2009 - 14 answers

A question and moral quandary from yet another sad virgin.... [more inside]
posted by anonymous on Nov 26, 2009 - 17 answers

Help! My new girlfriend is skeeved out by minorities. Should I break up with her? [more inside]
posted by Eleutherios on Nov 24, 2009 - 84 answers

Is it possible to ask someone out several months in advance? I've met someone great, but I've met them too soon! [more inside]
posted by anonymous on Nov 23, 2009 - 54 answers

So as fate would have it, I am sharing an apartment with a girl that I am very attracted to. And now it seems as if I've been perma-friended. (For the sake of discussion, lets forgo the “dating roommates is a bad idea” discussion.) [more inside]
posted by RandomGradStudent on Nov 22, 2009 - 118 answers

Late start at dating, and I'm worried that I don't/can't express attraction on dates or around people I like. Halp! [more inside]
posted by anonymous on Nov 18, 2009 - 8 answers

In the need of first date ideas, particularly in Portland, Oregon. [more inside]
posted by captainsohler on Nov 17, 2009 - 11 answers

Is it a bad idea to rent a room to a friend who expressed potential romantic interest once? [more inside]
posted by cheesecake on Nov 17, 2009 - 37 answers

I haven't had a crush since I was 14 and now I have a HUGE one. I have never had to be the pursuer before, but now I think I need to be. AskMeFi, teach me to flirt and pursue while still keeping me cool!! [more inside]
posted by SkylitDrawl on Nov 16, 2009 - 19 answers

I met the most beautiful geeky girl I have ever seen or imagined. Help me get her out of my head, please. [more inside]
posted by anonymous on Nov 16, 2009 - 66 answers

What resources would you recommend to a 29 year old woman who's got absolutely no game whatsoever and needs help with every aspect of the dating world, from meeting guys to keeping them? [more inside]
posted by tumbleweedjack on Nov 15, 2009 - 18 answers

Long distance dating between 2 single parents possible? I'm asking for my sister (who doesn't know I'm asking) because I want her to be happy but don't know if these relationships ever really work. [more inside]
posted by anonymous on Nov 15, 2009 - 18 answers

Is it OK to regularly hang out with one of your past girlfriends while dating someone else? [more inside]
posted by Askiba on Nov 11, 2009 - 38 answers

I'm part of a short-term couple. We both know it will probably end in about six months from now, due to a long-distance move. I feel that there's a multitude of things I can experiment with here, due to the short-term nature of the (non?)relationship. But what are those things? Also: I know that each relationship is different, but what are the general rules of such relationships, anyway? How am I supposed to be in love, without falling in love? What can I do to make the most of the time we have left? [more inside]
posted by anonymous on Nov 9, 2009 - 16 answers

Late to the dating game? So, I'm in my early 20s, graduated from college and now working. I have absolutely NO experience with guys, and I'm not sure how to gain some. [more inside]
posted by anonymous on Nov 5, 2009 - 29 answers

Depressionfilter: Help me understand a sudden increase in libido and its emotional aftermath. [more inside]
posted by anonymous on Nov 5, 2009 - 9 answers

I'm a young, "straight-acting", alternative guy who is tired of being single. Help me find a boyfriend! [more inside]
posted by mosherdan on Nov 5, 2009 - 23 answers

I have a first date with a girl coming up, which is awesome and I'm psyched. Only... I've never dated girls before! Help! [more inside]
posted by anonymous on Nov 3, 2009 - 9 answers

Let's say you remove geography from the equation in finding a potential partner. How would you go about it? [more inside]
posted by milinar on Nov 3, 2009 - 21 answers

Datingfilter: Did I just get blown off? Yes, there's more bean platiness to this. [more inside]
posted by anonymous on Nov 2, 2009 - 44 answers

Dating filter: How do you broach the “What are we doing?” question without striking fear into the hearts of all involved? Also, what do you do afterward? [more inside]
posted by fiasco on Oct 27, 2009 - 13 answers

Is this girl "out of my league"? I met an attractive (in every sense) girl recently, and we have a lot in common - except earning potential (and maybe to some extent family/social background). [more inside]
posted by KMH on Oct 27, 2009 - 51 answers

How do you phrase "are you into me?" in a non-terrifying way? [more inside]
posted by anonymous on Oct 25, 2009 - 22 answers

Was it a date? Last night I went out for a few drinks with a guy I've been interested in, but was it just friends hanging out? [more inside]
posted by hannahlambda on Oct 24, 2009 - 27 answers

How do you tell the difference between someone who's an extrovert and someone who's romantically interested in you? [more inside]
posted by anonymous on Oct 21, 2009 - 23 answers

I’m in the process of divorcing, and starting to date seriously again. The catch: I’m absurdly young to be in this situation. How and when to break the news to dates? [more inside]
posted by ripley_ on Oct 20, 2009 - 24 answers

Is she being honest/should I give up (online dating related)? [more inside]
posted by plungerjoke on Oct 20, 2009 - 31 answers

Is the idea of experimenting with a same sex relationship even smart when you aren't sure it is something you would consider in a long term way? [more inside]
posted by anonymous on Oct 18, 2009 - 22 answers

How do I properly initiate contact with a person who dumped me because he thought I may not sexually accept the way he is? How can I let him know that I'm the same way too? [more inside]
posted by anonymous on Oct 14, 2009 - 13 answers

Previously dated men, now wants to date women. Problem: I can't tell when women are interested in me or if they just want to be friends. [more inside]
posted by Eleutherios on Oct 13, 2009 - 17 answers