Does he?
June 20, 2010 6:38 AM   Subscribe

Dating advice for someone who hasn't really dated. *long winded, sorry*

I am 32 years old, female, divorced. I was married at 18 to the first guy I ever went out with, we drifted apart while I went to college and received my PhD... and now I'm single, and I have no idea how to date.

I've tried online dating, because I know I communicate wonderfully via online forums and chats. However, I am shy in public, and at a bar or other venue my friends tell me I sometimes give off an unapproachable vibe. I am told I am very pretty, if a little nerdy... and apparently I have incurable naivete.

Now, I've met a guy I think is very attractive, smart and witty - except I can't tell if he's into me, and whether or not I should pursue him.

We met at a friend's birthday party - he (let's call him Sam) is a friend of her fiance. While the mutual friend emphatically did not play matchmaker (something she told me she didn't want to do in case things potentially got awkward) she was very supportive and happy about the idea. It so happened that he added me as a friend on Facebook the first time we met, and there was very little interaction except for a chat on FB where he tentatively invited me to his birthday party (while amusingly enough telling me I was cute) - until another male friend from the same circle added me as well. (I know this sounds like a high-school dating drama, but please bear with me).

The second friend (let's call him Frank) apparently developed an interest in me, and both my friend's fiance, and Sam encouraged him to ask me out. Of course, because I like Sam, I turned him down, and Frank in turn told Sam to ask me out, which he did.

Our first 'date' was watching a soccer game at Sam's house, after which we walked to a local bar and got a drink. We talked, laughed, he touched my leg once or twice, and I got the distinct impression he was somewhat wary of us being in such a close circle of friends. He also made some 'teasing' remarks that may or may not have been funny that I chalked up to quirkiness. However, I was leaving for two weeks on work, and he ended up asking me out to dinner the next day because we wouldn't see each other for a while. Dinner the next day was great, and he came inside after dropping me off - without being asked. Again, sat on the couch for an hour or so, but he made no move t0 get closer, or flirt or touch.

As he was leaving, he gave me a tight hug as he had done the night before, wished me a safe trip, and was walking to his car when I decided to get a little bold. I laughed, and asked him if that was all I was going to get - a hug? He then came over, said 'I'd like you to say that again', and kissed me. It was ...sweet, no sparks or crazy tension... and I gave him a little push and he left. Later, I felt a little weird for being bold, so I texted him apologizing for being forward but saying I enjoyed it! His response? 'Well it made it much more memorable, so win win. :) Good nite!"

Well, bummer. I didn't know how to interpret that. Since then, he's commented/ liked a couple of my FB statuses, I saw him online once late at night and we had a somewhat short/ awkward chat about soccer because it was late and he was going to bed, I've been out of town and he texted me during a soccer game - 'Go USA!'

On my part, I am intelligent, maybe slightly boring, but naive and honest. For example, I had noticed one or two of his FB friends were people I knew from being on Yelp - when I mentioned that to him, I noticed later that he had hidden his friends list.

I apologize again for this long-winded rigmarole, but this is reminiscent of almost the last 6 or 7 dates I've been on. Is he interested? What do I do to find out? Not to sound arrogant, but my looks, especially in this case because he's met me a couple times before, aren't usually an issue. I just... don't know. He's divorced as well, and a full 10 years older than I am, although he is Asian, and looks half his age.

I think I'm going to break down and ask what I should do, and if he likes me... because I haven't felt this strongly about someone in a while. He's an excellent writer, something I think is sexy. He's clean, witty, and honest. He cooks. He is kind to people he's friends with. Perhaps he values his privacy, and doesn't want to be talked about in this close circle of friends. Perhaps it’s a cultural thing – my Asian friends tell me Asian men are a little slow to respond. Perhaps he’s just not into me – which I am fine with – I just want to know!

Opinions? Thank you much. I don't think I like this insecure me, and I know I am being completely over-analytical... but I am sick of being lonely :(
posted by anonymous to Human Relations (15 answers total) 3 users marked this as a favorite
You don't get kissed by guys who are not into you. Quit bean plating and relax. He'll ask you out again as soon as he knows you're home.
posted by wwartorff at 6:46 AM on June 20, 2010 [2 favorites]

Perhaps he’s just not into me – which I am fine with – I just want to know!

He kissed you and called it memorable. I think there's only one way to interpret that; he wants to do it again.
posted by Hiker at 6:48 AM on June 20, 2010 [2 favorites]

You're out of town! What more are you looking for from a guy you've had one date with? Relax, keep up the communication while you're away, and ask him out on a date for when you get home.
posted by ThePinkSuperhero at 6:49 AM on June 20, 2010 [2 favorites]

"Later, I felt a little weird for being bold, so I texted him apologizing for being forward but saying I enjoyed it! His response? 'Well it made it much more memorable, so win win. :) Good nite!"

Well, bummer. I didn't know how to interpret that.

Speaking as a guy, that certainly sounds to me like he enjoyed the kiss and enjoyed your company.

I think maybe either you haven't learned to give out the "come and get me" signals that many women use to signal their interest or else the guy hasn't learned to read those signals or else he's shy or uncertain about reading those signals.

The easiest way to find out is to ask him out for another date. If he accepts, but doesn't put any romantic moves on you, try starting something yourself. I know that back when I was single, I never had objections if a woman I was on a date with wanted to kiss me.

There is always the chance that he won't be interested. In that case, move on to the next guy and try again. I know it might seem scary to take the initiative and risk rejection, but remember that guys have to take that chance all the time. If we can do it, you can do it.
posted by tdismukes at 6:58 AM on June 20, 2010 [1 favorite]

You're never too old to admit to someone's face that you like them. And people don't generally kiss someone they dislike and then maintain contact afterwards, do they?? Stop overthinking.
posted by fso at 6:59 AM on June 20, 2010 [3 favorites]

ThePinkSuperhero has it.

Look, he's interested. Just a little shy himself, possibly because he can tell you're a little anxious about the situation too. He's being awfully sweet about it, from what I can tell. When he wants to see you again when you get back, he'll get in touch. If he doesn't, it's okay for you to call and say "I'd like to see you again. Want to grab dinner tomorrow?" If, for some strange reason, he's changed his mind, you'll be able to tell by the sea change in how he's communicating with you.
posted by knile at 7:02 AM on June 20, 2010 [1 favorite]

Yes, he does seem to like you. Atlhough, it doesn't hurt to ask him directly, if you want to resolve this in your own mind.
posted by SpacemanStix at 7:05 AM on June 20, 2010

You don't have to pursue him. He likes you, and it's his turn. Give him a chance to pursue you . I know it's painful to wait for days, but it's worth it. If you are overeager, you may lose his interest. Yes, I know the men of Mefi (and all men) tell you how great it is when a woman asks them out, and of course it feels great, but where does it lead?
Please feel free to memail me.
posted by uans at 8:04 AM on June 20, 2010 [1 favorite]

Oh dear God.

You like him and all indications are that he likes you. When you get back to town, ask him if he'd like to do something that week. Nothing ventured, nothing gained. Minimising risk in romantic endeavours has not, historically, proven to be a winning strategy.

I do not believe in playing dating games. If you like someone and want to see them, I see no upside in pretending anything else.
posted by DarlingBri at 8:10 AM on June 20, 2010 [2 favorites]

It made me laugh when he said 'Well it made it much more memorable, so win win. :) Good nite!".

Its a bit better than when someone told Ross on the TV show Friends that they loved him and he said "Thanks!" and that was it. Or maybe it was different character or show - I don't watch TV anymore.

Fuzzy answers beget fuzzy replies and so on.

I'm also single now after many years together with someone and all I know is that I don't want to play any games whatsoever.

To me its about communication. I'd rather be with someone direct and clear. Relationships are complicated enough and require strong communication. Don't start out on the wrong foot.

I'd say stop tippy toeing around things and be clear as possible.

Also, start reading about relationships and define what makes a healthy relationship for you.

You'll understand things better and it will clarify your goals. If you don't do that, you will learn by trial and error or from advice from friends which may or may not be helpful - the hard way.

Its a win win situation I think!
posted by simpleton at 9:11 AM on June 20, 2010

It sounds like Sam is into you and that's great! However, since you are new to dating after a long time, I think it's important to put the one date and kiss in broader context. You might go out with Sam a few more times and one of you might lose interest, or you might date for a year. There's no way of saying. At this point you've just gone out on one date that happened to end with a kiss.

This part gives me pause for two reasons:

The second friend (let's call him Frank) apparently developed an interest in me, and both my friend's fiance, and Sam encouraged him to ask me out. Of course, because I like Sam, I turned him down, and Frank in turn told Sam to ask me out, which he did.

Since you're just starting to date after a long while, it's good to go out with a variety of people until you meet the right one, even if you are not smitten at first sight. You never know who you are going to click with, you never know when Sam might disappear, since you really don't know him yet, and dating itself gives you practice feeling comfortable making small talk with strangers. It also gives you a way to gauge how much contact is too much. The more you casually date, the more you'll find the right balance.

Also, Frank and future Franks don't need to know why you're turning them down. If a guy turned you down, would you want to know it was because he was interested in Jane?

It sounds like you are off to a great start with Sam! While I agree that playing games is silly, it's also important to convey that you're laid back enough to go with the flow. You made a major move on your first date, after all. See what he offers next.

And don't say no to Franks that come along in the meantime.
posted by vincele at 9:50 AM on June 20, 2010

I think I'm going to break down and ask what I should do, and if he likes me.

Yes. At least, I'd do that. Is it a bad thing to do?
posted by westerly at 11:38 AM on June 20, 2010

Is it really game-playing to hide how desperately lonely and insecure you are, or is it common sense? The OP was delighted that Sam, on their first date, came in without being asked. Really? Isn't that cause for concern? She is disappointed that he didn't make a pass at her on their first date. Of course, if the OP's desire is simply to get laid immediately, then fine. More power to you! She asked for a kiss....was made to ask twice for that kiss...and now the OP is wondering why Sam is not making much effort to contact her.
Loneliness is the one of the greatest pains imaginable, and the sight of pain drives people away. Hide it. And if that's game-playing, so be it.
posted by uans at 2:16 PM on June 20, 2010

When in any dating situation where I feel like I'm not reading signals correctly I always just ask.

"Hey, I like you but I am bad at reading signals, are you also in to this?" and as far as physical contact I also sometimes say, "I would really like to makeout with you." Not the most romantic but it gets the job done until you have time to learn what the other initiating physical stuff looks like.

You'd be surprised how many find this approach refreshing and will be pretty open and honest. I also recommend putting a daily limit on dating agony. I would allow myself about 20 minutes to freak out over the subtext of an e-mail and then I would just try to put it out of my mind and quit worrying it. Otherwise I found I was tending towards having relationships that were mostly in my head.
posted by Saminal at 2:44 PM on June 20, 2010 [1 favorite]

Jesus Christ, does he like you. Touching your leg? That's what guys who like you do.

It sounds like he is a bit awkward and shy/overthinking too, so I think that if you continue to be bold and confident, good things will happen.
posted by mreleganza at 7:07 PM on June 20, 2010

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