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It's beginning to look more and more as though a friend is trying advance our relationship into something more. And I'm not sure how I feel about it.

Background: I met this girl about 3 years ago through some mutual friends. I was attracted to her initially, but she had a serious boyfriend and my dating life was a wreck, so I didn't pursue her. About a year after that she got pregnant. Since the baby was born, she and the father have split up amicably... but he still lives in a separate room at her house.

During the last year I began to notice odd little hints coming from this girl. At times she is bitingly sarcastic with me (which is fine; it's how she interacts with most of her friends), but other times it took on more flirtatious overtones. She would make little comments that could be construed as her coming on to me, but they were vague enough that I couldn't be sure. I just assumed that I was reading too much into it and tried to ignore it. Still, it kept happening. Even my other friends began to notice and wonder. She began to tease me about how we don't hang out enough, just the two of us. She began trying to make plans with me all the time despite the fact that I was never free at the same time she was. Still, I told myself that there was no way she was interested and she just wanted to hang out as friends.

So last Monday, after a dinner party at our friends house, she and I walked out to our cars. She was tired so I simply said good night and walked off to my car. She suddenly made a quip about wanting to go out to dinner this weekend. I finally agreed to meet up, still thinking this would just be a friendly outing. She suggested pizza, and I agreed for tonight (Sunday).

Now here is where my alarms are really going off. She sent me a text saying she still wanted to go out, but wasn't in the mood for pizza. No problem, I replied. I asked if she had any suggestions. She decided on a place I'd never heard of. Looking at the website, I can see this is an ideal place for dates with a darker, quieter atmosphere. The food is decidedly more upscale - it's just the type of place you would take to impress someone.

So here are my issues:
First, I'm not sure what's going on exactly. Is she into me? Is she just a friend and I'm reading too much into it all? It's starting to seem like too many hints and coincidences, but the more logical part of my brain makes me think it can't be.

Second, if she is into me... what should I do? I do find her attractive and normally I would definitely be interested in dating someone like her. But I'm not 100% convinced this would be a good idea. My main issue is that she's a single mom with a complicated relationship with her child's father. I respect the hell out of her and what she does. I just don't think I'm ready for that level of complication. My work situation is dodgy and I'm still looking for something better. I'm awkward with kids and I don't know how to act around her daughter. I'm full of self doubt and have a tendency to be a little flighty at times. I worry that I don't have my act together well enough to even contemplate this type of relationship.

My head is spinning with this. I'm just not sure, so I'm turning to you guys. Opinions? Advice? Therapy?

I say go for it. Nothing ventured, nothing gained. It's just a date after all.

Oh, sorry, I forgot to add one more concern: if this doesn't turn out well, we have a lot of mutual friends and it could make things ugly. That was my only other hesitation and why I'm not taking it lightly.

It's still just a date. You aren't asking her to marry you or something.

she's a single mom with a complicated relationship with her child's father

ThatNickGuy just finished semi-dating a single mom with complicated baby daddy issues. He's the one that should give you some advice right now.

phil said:

she's a single mom with a complicated relationship with her child's father

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And my mind's... tellin' me no.
But my bodyyyy's tellin' me ye-heh-heeess!

SeraRelm said:

And my mind's... tellin' me no.
But my bodyyyy's tellin' me ye-heh-heeess!

Click to expand...

point retracted. hit it and quit it.

SeraRelm said:

It's still just a date. You aren't asking her to marry you or something.

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That's true. I'm a former commitment-addict who would always get into longer, more serious relationships. My default approach to any date is to think about if it has long term potential. You might be right in that I shouldn't try to look so far ahead and just stay in the moment.

phil said:

she's a single mom with a complicated relationship with her child's father

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Haha. At first I was going to name this thread "It's a trap! (maybe)"

You're going to dinner with a friend; not launching the damn space shuttle.

Just go.

^That. If you're not even positive what it's about, just go.

Mathias said:

You're going to dinner with a friend; not launching the damn space shuttle.

Just go.

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There isn't even one left to launch

And yes, it's a date. Go have a nice dinner.

'Preciate the tagging, Sheg, but not really sure what advice I can give. The dating didn't honestly last very long. One date, in fact. She still had a lot of issues with her ex-husband and in fact, they got back together.

In this case? My advice would be to focus on her and the potential dating/relationship with her, first. Don't expect to be some kind of father figure immediately because right now, it's about building a relationship between you and her. In fact, I would even put off meeting her kid for at least a little while. That gives you both a chance to see how things are between the two of you, and also helps her see whether she is ready or comfortable for you to meet her daughter. Let it be her decision, of course.

Basically, what I'm saying is this: focus on the dating between you and her. Don't overthink anything else. She's the mother. Let her think about that sort of thing for now.

Also, advice on how to be less awkward with kids? If they're still young, get down on the floor and play with them. Play is the biggest social interaction for children and they'll respond to that best. You don't even have to do much. Make a few funny faces or a funny voice. Even play blatantly dumb, like asking them something they know what you say isn't the right answer. Trust me, kids will eat that up.

Meh. Just go with the flow. If you two hit it off, great. If not, tell her that you're not interested in being more than friends with her and move on with life.

Yeah, there are risks you are opening yourself up to by dating her, but they aren't big risks right now, and you need to realize that she's opening herself up to some risks as well - she's already gone out on a limb. Date her a few times, see if there's something there, and then evaluate whether the other issues you bring up are really going to be a problem. She's not perfect, you're not perfect, but you might have a good time together, even if only for a little while.

Quick Update:
Thanks for all the advice. I realized that I was over thinking things and just went with the flow.

The night went well. We enjoyed dinner, talked, and flirted for hours. It was nothing hot and heavy, just seemed like a good basic first date.

Then, as the night drew to a close and I walked her to her car, it was as though someone poured ice water on her. The good vibes disappeared in an instant, and it was as weird/platonic as could be. I'm not really sure what that was all about. But really, I'm done worrying about it.

Thanks again everyone.

Now send her a text, asking when you can tap that.

IMO just go and have fun.be yourself.

Go there without expectations and if something comes up be honest about how you feel about the mutual friends... Don't mention the dude.... At least not for today.

Also make sure mention that she looks good if she goes though the trouble to look really good for the date....


Lsms tap dat

Just Some Guy said:

Quick Update:
Thanks for all the advice. I realized that I was over thinking things and just went with the flow.

The night went well. We enjoyed dinner, talked, and flirted for hours. It was nothing hot and heavy, just seemed like a good basic first date.

Then, as the night drew to a close and I walked her to her car, it was as though someone poured ice water on her. The good vibes disappeared in an instant, and it was as weird/platonic as could be. I'm not really sure what that was all about. But really, I'm done worrying about it.

Thanks again everyone.

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What? ..What? ...WHAT?!

No.

No no no no no you're doing this all. wrong.

Where's the insane overanalysis to the point or paralysis? The exposing of deep-rooted neuroses? The therapy jokes! WHAT HAVE YOU DONE

YOU BROKE HALFORUMS

YOU MONSTER

They're not even bringing up previously unexplained psychological problems where we promptly suggest therapy!

How else is this damn thread going to make it past two pages?

Ok, I'll help throw some anxiety into him

Just Some Guy said:

Quick Update:
Thanks for all the advice. I realized that I was over thinking things and just went with the flow.

The night went well. We enjoyed dinner, talked, and flirted for hours. It was nothing hot and heavy, just seemed like a good basic first date.

Then, as the night drew to a close and I walked her to her car, it was as though someone poured ice water on her. The good vibes disappeared in an instant, and it was as weird/platonic as could be. I'm not really sure what that was all about. But really, I'm done worrying about it.

Thanks again everyone.

Click to expand...

So, there was never any concrete indication that it was a date, right? And you went out and had a good time with flirting and the like. Still no concrete confirmation of it being a date, or of your/her feelings. Then at the end she gets cold/icy. Three possible explanations (there are others):

1) She's got a complex situation and got cold feet near the end as she started thinking about the life she was going back to (kid and baby daddy living at home.) Boring.

2) She was setting you up to make a move on her and/or announce your feelings, and when you didn't she got pissed/offended/embarassed. Anxiety

3) Reindeer games. Super Anxiety.

Well, you still went out and had a nice date-type-thing. Minor victory!

BBT.

Just Some Guy said:

Quick Update:
Thanks for all the advice. I realized that I was over thinking things and just went with the flow.

The night went well. We enjoyed dinner, talked, and flirted for hours. It was nothing hot and heavy, just seemed like a good basic first date.

Then, as the night drew to a close and I walked her to her car, it was as though someone poured ice water on her. The good vibes disappeared in an instant, and it was as weird/platonic as could be. I'm not really sure what that was all about. But really, I'm done worrying about it.

Thanks again everyone.

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It's pretty obvious isn't it?

She had to take a shit really, really bad.

Just Some Guy said:

Then, as the night drew to a close and I walked her to her car, it was as though someone poured ice water on her.

Click to expand...

Sounds like she was suddenly nervous and self conscious. Don't read anything into it.

She went out on a limb to ask you out. If you enjoyed the main part of the date, seriously consider asking her out again, she'll be looking for you to make the next move if you want to. If you don't, she might take that as a rejection and look elsewhere.

Don't assume that the end of the date was meaningful, and don't assume that she's not interested, and don't assume that she'll make another move if she is interested.

The ball is in your court, decide what to do with it.