Help me sort out this budding relationship
September 28, 2009 7:28 PM   Subscribe

I am a bit of an inexperienced dater for my age but after 3-4 dates am feeling good about a new squeeze. Help me figure out the next move to let her know I am interested while still playing it cool.

A little history about me: I am a guy, late 20's, gainfully employed in a lucrative profession and living in a major U.S. city. I am tall, reasonably attractive, and these days very fit. Though, my dating and relationship history betrays the current merits of my situation. Growing up I was always overweight and lacked confidence and self-esteem. I also developed a pretty serious affair (or addiction, if you prefer) with marijuana in my teenage years which eventually blossomed into experimentation (and limited abuse) of various other substances through college and into my mid-20's. For most of my life I was also relatively introverted, timid and shy, which of course was not helped my copious marijuana smoking, which made me even more reclusive and introverted usually. I did have a fair amount of guy friends, so I was not a total social outcast.

With that backdrop, I didn't date at all in high school and only randomly in college (organized social fraternity events mainly). I lost most of my excess weight in my earlier years of college, but still lacked confidence and maturity, so things didn't really turn around for me. I didn't lose my virginity until the latter years of college, but that was basically a fluke anyway.

Post college, I dated randomly, but never had a girlfriend, and never really made it past 2 casual dates with the same person, usually ending in the "let's smoke weed Friend Zone" or in complete rejection. There was a period in my mid-20's where I didn't really date at all for a solid 2 years. Though, I did have a handful of random semi-drunken bar-club type hook-ups, which have sort of given me enough sexual experience to not be a complete noob. Generally, I am not worried about my performance in the hook-up/sex department, despite my limited experience. It is more the relationship/dating aspect that puzzles me.

In the past 2 years, I have really cleaned up my act a lot. Completely stopped all drug use, ditched those friends that were bad influences on me, and have found a happy median with marijuana where I smoke it a couple times a week but it doesn't control my life like it used to (not interested in quitting). I drink socially in small quantities, though never really had any "problem" with alcohol. During this 2-year catharsis, I started exercising (lifting and running) regularly, and hence I am in excellent shape now and, more importantly, all of these life changes have given me a whole new outlook on self-esteem and confidence, etc. Also, I'm really thriving at work, which completes the picture nicely. In short, I am at a great place in my life, except for a lack of girlfriend.

I am not desperate though. In the past few months, I have been pretty successful at getting dates, even getting asked out myself, and for the first time it has been me sometimes rejecting someone else and feeling like I can be selective, which is a great feeling. I am also not really afraid of rejection anymore, as I realize it is a natural part of dating. I am not into games though; I am usually pretty straight-forward with people.

Anyway, so three weeks ago, I met this awesome girl, and it is going really well after 3-4 dates, besides for one really weird quasi-date (as I will explain). She is 2 years younger than me, also a hard working professional, lives close by, and we have a ton of similar interests. I am also really attracted to her mentally and physically, though I'm not sure if she fits the classic definition of super-hot (so she isn't pretentious or all about her looks or anything like that), which I actually prefer.

So, we met on a craigslist. She posted in the platonic section saying she was going to a music festival alone (I subsequently found out that she recently moved to the city I live in). I was also going to the same event alone, and we emailed back and forth and made very loose, non-specific plans to try to meet up. We ended up exchanging a couple random texts during the event, but missed each other since it was a very large event with tons of people, and we hadn't exchanged pictures so neither of us was trying too hard.

We exchanged some more texts/emails in the days that followed (in a pattern of me initiating and her quickly responding), and it turned out we worked near each other also, so I invited her for a quick lunch the next Friday. We had a great conversation, shared some laughs, but it ended all too quickly, since we both had to return to our respective jobs. She mentioned that she was going to another event the next day, and I asked her if she wanted to go with me, to which she enthusiastically said yes.

We met up the next day, walked around a bit and meandered to the event. The conversation was fun and we were lightly flirting, light touching, etc. I thought things were going great, but then as soon as we got to the event she said she saw someone she knew and would "come find me later." A few minutes later, I saw her talking to some Other Dude, and I decided to give them space. A half an hour later, she still hadn't come to find me yet, and I was walking around and saw her standing alone. I came over thinking she was by herself, and at first she seemed really happy to see me and flirtatious (e.g. she had someone take pictures of us and was hugging me after that) but then after a few minutes she started acting really strange. She kept making thinly veiled comments that I would have more fun dancing (she was away from the dance floor when I found her), and things that led me to believe she wanted me to go away...too late; then the Other Dude came back with drinks for her and him. The drink line was long, so the timing all makes sense, that she tried to get me to leave before he returned.

She awkwardly introduced us, and pretty quickly I started feeling like the third wheel. I learned that she had met Other Dude the weekend prior at the same event that I missed her at. It is unclear to me if she knew that Other Dude was going to be at this (much smaller) event, or if she had plans to meet him, or if it was just happenstance. Other Dude was pretty flirtatious with her, kept touching and grabbing her, trying to kiss her and dance closer. I could see her pulling back though and pushing off his advances a bit. Though, she didn't totally push him back, just wouldn't let him cross the line from flirtation to outright grinding/kissing. Way too much ear whispering and arm around her though, and it was just incredibly awkward for me. I tried to steal her attention a couple times, but she seemed more interested in talking to him and at one time when the Other Dude went somewhere else (to pee or make a call or something), she denied me when I suggested we go dance at a different part of the event (hoping to get away from Other Dude). Also, just to add another level of complexity, Other Dude apparently was married (or at least had a wedding ring on). He was actually a nice guy otherwise and was cordial to me, but it was just very weird. He did not seemed phased that I was there, however, so I doubt they had a formal date arranged.

So, after enduring the third wheel situation for sometime, I realized Other Dude wasn't going anywhere. Since it wasn't clear what their involvement was together or whether they intended to meet, I gave up trying to be assertive and "cutting in" or anything like that, so I prematurely said goodbye and left to go dance on my own and meet some other people.

I bumped into them again as the event ended and everyone was stuck on line for some period waiting to leave. During this time I overhead Other Dude call his wife with some lame excuse of how he would be "late" that night or something or other, and the two of them seemed like they were leaving together.

The next day, I sent her a text message pretty much saying, "Wish we could have chatted more, but you seemed preoccupied." She wrote back (quickly) saying she had a good time with me "but was just having a little fun." She didn't offer any further explanation or apology.

I waited a little over a week to let things simmer a bit and secretly hoped she would ask me out, since I felt like she screwed up the last date, but I didn't hear from her. So, I texted her again asking her out to dinner this past Friday night. She (quickly) responded affirmatively and seemed really excited.

So, we have dinner on Friday and things go great. Excellent conversation and laughs, and right away she is being very flirtatious. After dinner, we go to get a drink, and she is practically all over me. We end up back at my place and end up staying up the whole night making out and chatting. Heavy petting but no climax or nakedness. She says she is really into me, etc., and vice versa. We agree (at my suggestion) to go clubbing together the following night (Saturday).

Clubbing goes great. We were all over each other all night, grinding and kissing, and had a blast. She seemed REALLY into me. We go our separate ways afterwards though, because it was already the next morning when we left and we were both exhausted.

This afternoon (Monday) I send her a short flirtatious text (with no indication of any future plans). She writes back very quickly with the same type of text, terse and flirtatious.

So, here we are tonight. I want to ask her out again, hopefully for this coming weekend, but I am not sure how long to wait, or whether I should see if she asked me out. If you followed along in the story, I have always been the one to initiate plans and texts, but she has been very receptive and always responds quickly. Is that just her personality, or is this part of some game in which it is expected that the male be the aggressor? I thought about calling her, but we both are very busy and have mutually discussed how we generally prefer text and save talking for in person.

I am trying to play it cool and not quite sure how to proceed. I want her to know I am interested, but don't want to move too quickly or appear desperate at all. Help me out, meta-hive-mind!

Also, given the ambiguous situation with Other Dude, at what point would it be appropriate to ask her if she is seeing him, or seeing other people for that matter? Considering Other Dude was presumably married, would her actions be a red flag? I would like to give her the benefit of the doubt but don't want to become involved with someone with that type of moral turpitude.

Long post, appreciate those who take the time to read and respond.
posted by pseudomouse to Human Relations (9 answers total) 4 users marked this as a favorite
 
"Where would you ideally like to see this go? I really dig you."

Hemming, hawing, and beating around the bush, as it were, are antithetical to your desires.
posted by notsnot at 7:42 PM on September 28, 2009 [4 favorites]


Wow, that was a long way of saying "I dig this chick I met, and she seems to dig me, but I know she's still playing the field - what now?"

Have fun with her. It sounds like she's genuinely "just having a bit of fun", and was sort-of enticing you to do the same. If she wasn't at all into you, she wouldn't agree to Friday & Saturday dates, nor would she have gone back to your place for an all-night heavy makeout session, etc.

Have you considered trying to meet other people as well? If you're putting all your eggs in one basket - so to speak - you're going to be hurt every time she says she has other plans. Even if they're harmless "girls night out" events, you might end up getting paranoid thoughts about "what's she really doing?" and therein lies dragons, my friend.

Frankly, this girl doesn't sound at all ready to settle down in any form - so maybe try to find some new people out there. If you prefer the online dating route, try OkCupid or PlentyOfFish (or similar sites). You said yourself that you're relatively inexperienced for your age. So, get out there and mingle and don't get too serious with anyone for a little while. You need some fun, just like this girl.

Good luck!
posted by revmitcz at 7:43 PM on September 28, 2009 [1 favorite]


She's just having fun. You could easily date her regularly.

I would not date anyone who was also dating someone who was married. That's one glimpse you've had into her true character so far.
posted by srrh at 9:29 PM on September 28, 2009 [2 favorites]


She's just having fun and seems like she doesn't want to be tied down. She just moved there and is probably just playing the field, so I wouldn't get too invested in this just yet. You can ask if she's seeing other people, if you have exclusivity in mind. Otherwise, just date her casually and leave it at that --if you feel emotionally able to handle that. And it's not clear if you are or not since you seem eager to attach.

"we both are very busy and have mutually discussed how we generally prefer text and save talking for in person"


Another possible hint. Perhaps she's juggling several and talking would be too hard to keep up with.
posted by cmgonzalez at 9:43 PM on September 28, 2009


Oh god, I hate women like that. Her behavior at this festival seems like pure tease. Flee.
posted by paultopia at 5:15 AM on September 29, 2009 [1 favorite]


She seems to like you, but she also seems to like Other Dude more. However, it sounds like Other Dude could be history, so you could easily just keep having fun with her. However, it sounds like she doesn't want to commit to anyone and is keeping her options open.
posted by maryrosecook at 7:19 AM on September 29, 2009


She is an attention whore. Congratulations! This will not end in a relationship.

However, you could most likely continue to get toyed with for as long as you feel like...
posted by shownomercy at 9:57 AM on September 29, 2009 [4 favorites]


Wear a rubber.
posted by Jacqueline at 8:43 PM on September 29, 2009


Um, you are way WAY over-analyzing this. This is perfectly natural for someone who's not done a lot of dating, but it also means you're kind of already invested in this thing as a "budding relationship" (which it most likely is not).

Go ahead and make plans. Very generally speaking I've found women prefer men to be the aggressor and to suggest the plan. This isn't a hard and fast rule, just a general guideline. But don't be the guy who says "I don't know, what do you want to do?"

But dating is of course a numbers game and you will most likely date a bunch of people before you settle into something long-term. Don't get too invested until it's really warranted and the feelings are mutual.
posted by lackutrol at 12:41 PM on October 2, 2009


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