Dated her previously to no avail, now going out again -- advice please! (LONG)

I’d love your input on this, although I admit this is also a cathartic rant of sorts and something of a spinoff from Lizard’s thread.

I met a woman, let’s call her “Angela”, a year and a half ago at an alumni mixer through a mutual friend I knew from undergrad. Angela had recently arrived in the city, having just finished grad school. I intuited that she was interested in me, although she might very well just have been networking. (She’s foreign, and we’ve had our fair share of interpersonal clunkiness due in no small part to our differing cultural scripts.) Regardless, my sights were set elsewhere at the time, so I didn’t keep up ties.

Then, last summer, we ran into each other again and became very friendly, socializing frequently in small groups and chatting regularly on the phone. We eventually went out on a proper date, and although she was initially surprised when I made a move at the evening’s end, she clearly didn’t mind.

On our next date, she mentioned she had once been married before. Between that, and a conversational tangent in which she asked how I perceived her, I realized she was trying to send a message. But I elided the conversation elsewhere in the hopes that I could will it away. I then foolishly assented to joining up with our mutual friend for some dancing. The night quickly soured into an agonizing third wheel nightmare. I wore my game face, but washed my hands of her once she stopped returning my phone calls.

When I ran into Angela at a cocktail party last fall, she seemed very ill at ease around me and left soon after she arrived. Her loss. That same night met the woman who was to become the love of my life.

This January, I got an amusing call from Angela wishing me a happy New Year – basically “hey there, long time, no chat”. We talked briefly, and I made brush-off “let’s get everyone together for dinner sometime” plans. Then a month later, the love of my life broke my heart and left me. And soon I found myself, through re-intersecting social circles, running into Angela quite a bit.

And it was all a very good time – we were talking with more comfort, frankness, and passion than before. And then we began seeing each other – non-romantically – quite frequently each week, for a quick dinner, or movie, or whatnot. I finally asked her, “When we were going out last fall, I got the feeling that you were uncomfortable with something, and I’m curious what that was.”

She laughed about that being a conversation for another night, but yes, she had been meaning to talk to me and time simply slipped by. Since then, we’ve basically been going through the motions of a good friendship with some healthy sexual tension. I’ve also been privy both to anecdotes about guys she has not been interested in who nonetheless pursued her (Danger, Will Robinson!) as well as laments to her girlfriends (with me in the conversation) about how guys are always into them and never her.

Last week, on her otherwise-unobserved birthday, I surprised her with a little present relevant to our recent conversations. Before I left her apartment, amidst much “Kiss her, you fool!” sentiments ringing in my head (no doubt whispered sotto by Gallic crustraceans, whom I promptly ignored), she was fishing for compliments about her looks – which I certainly was not going to provide, even though I find her quite beautiful.

Finally, this past weekend, she had people over to her place for drinks. As night wound into day, only we two remained. I put her to bed, exhausted as she was, and silently agonized over what the hell I was doing there. I finally kissed her, and she kissed back. “Can I call you tomorrow?” I ask.

“Sure,” she mutters, nearly asleep.

“Right, but will you answer the phone this time?”

We laugh, I leave, we talk yesterday and make plans for a drink tonight.

Long story short (too late), here’s my question: I’ve long outgrown those high school days of talking my feelings to death with a woman to whom I’ve got no emotional claim. And indeed, I’ve had good luck in recent years of simply making my move and seeing if it sticks. But since I’ve gotten ample mixed messages from her, how should I make clear that I enjoy her company, find her attractive, hope she feels the same thing, and would like to pursue something more – without any expectations beyond the moment?

Disclaimer: Providing advice 'cuz you asked… This is ALL ENTIRELY my opinion, based on the women I’ve encountered in my life.

I’m not sure why you’re feeling mixed signals. Nothing in your post sounds especially that way to me. I see a lot that sounds like a go-ahead, and nothing that sounds like a go-away particularly. The one thing you mention that sounds that way on the surface is her talking about other guys who pursued her unwantedly… But in the past, I’ve always found talk about guys who didn’t measure up usually equates to “you do, so make a move, moron.” The laments to the girlfriend also strike me as NOT a mixed or negative signal, but a “hey, I’d LIKE a guy to be interested in me… Maybe the one right here listening to this” signal. In short, listen to the crab…

OTOH maybe something you didn’t write is holding you up? I’m very curious about this:

Why were you “certainly not” going to provide 'em?

As for “how”… listen to the crab. When another moment (sounds like there have been a few already and I’ll bet another will come shortly) strikes, friggin’ kiss her, fool!

I know, I know… It would be much safer and more comfy to just ask her. “So, X, do you see anything happening between us besides friendship?”… Don’t. IMHExperience, that’s a romance-killer and you are pre-ordaining a “no” answer – even if it woulda been “yes” until you showed yourself to be a chicken-hearted, unromantic dork (in her eyes).

In a worst case scenario, you kiss her, she pulls away and says “no, no, no”… I think it very unlikely (again, assuming your post is accurate and complete), but should it happen, then be honest. Say “look, I thought I was getting some signals and didn’t know any other way to sort it out…” and make clear you’re cool with it not being, end of story.

PS - In case you haven’t guessed it, I had a very similar situation once. Never did anything about it – too much of a chicken-hearted, unromantic dork, you see. It remains a big regret, particularly since I found out later (after she was safely married and genuinely off the market) that I was THIS CLOSE to something if I’d just gone the extra inch and kissed her… Do you recall the scene in Citizen Kane where the Bernstein is talking about the girl he glimpsed once and never another day passed that he didn’t think of her? Okay, now you’ve got the feeling…

I hear ya, you loveable Lectroid madman, you. And sure, maybe I’m just looking for validation. :slight_smile:

Basically, I went with the flow the first time around – no deliberation, only action. And I even cleanly cut myself off when the action proved fruitless. But now, given that I’ve already made the bold ploys the first go 'round, what qualifies as fresh and “take charge” at this point? (And totally, I saw her various anecdotes and laments as both negative and positive signals, hence my belief that at the very least, there’s something to work with here.)

UPDATE: she just called, and probably won’t be able to make tonight (something that I knew about), and it sounded like she’s thinking of this as a formal conversation we need to have. (My jokey comments about “finally having that conversation” seem to have been counterproductive.) Hmm.

My o my. Look like the boy too shy. You wanna kiss the girl.

Heh. I’m thinking my hyper-verbiage drowned out my key points:

  1. “Angela” and I went out last fall.

  2. We kissed plenty.

  3. She stopped calling, presumably because she feared my expectations, or wasn’t ready to date at the time.

(Or she doesn’t see me “that way” and only made out because she’s polite. Heh. It’s POSSIBLE she thought I wasn’t interested because after our second – and final – date with the third wheel annoyance, it was impossible for me to act like I was on a date and so I didn’t kiss her goodbye. It was awkward enough, given that her friend was standing right there.)

  1. After a period of no contact (I was off the market for a while), we’ve re-established a much more emotionally intimate rapport.

  2. The other night, we kissed again.

Granted, we were both really tired and she was somewhat tipsy. While there was certainly no repulsion on her part, neither do I sense any great enthusiasm. I also attribute some of her ambivalence to her generally aloof nature (something I can relate to, up to a point), as well as the fact that she was recently divorced, at a relatively young age.

  1. Given that she thinks I want to “have a conversation”, how do I untangle this needlessly convoluted mess into something more enjoyable?

I pretty much know what I wanna do, but I’d still enjoy getting my fellow Dopers’ diverse perspectives on the subject. :slight_smile:

Dear heaven. Quit overthinking the whole mess and ask her to go steady with you. Or go to dinner with you. Or go to Makout Pointe with you. Whatever it is you want out of your relationship with her. Leave the overanalyzing and excessive verbiage until after there’s a subject for it.
Go get her, tiger! :slight_smile:

Don’t let her break your heart.

Sure, she likes you. She enjoys spending time with you and she wants to kiss you. But she’s playing games with you. Most of all, she’s with you because she wants to hear how dazzled you are by her beauty and charm. I did the same thing to a guy when I was fifteen. You’re what’s available right now, and you’ll do, but I doubt she realizes what a treasure you probably are.

Hey, that crab wasn’t French; he was Jamaican.

Well . . . all I can add is I wouldn’t date the man I’m now going to marry for three years. That’s right, three years – we’d get together occasionally for lunch or drinks, always had a great time, several times did some kissy face stuff but I still wouldn’t date him because I was scared.

So – maybe she’s scared. Maybe it’s the cultural difference. Only you can decide if the potential reward outweighs the potential rejection. Clearly for us it did.

I am not the optimist DrLizardo is. I will try to be fair in myassessment of this situation though. As I see it, after considering everything you have said about this woman in this thread there are two possibilities:

1 - The optimistic scenario. When you dated before she was immature and not ready for a “relationship,” or at least one with you. Immaturity is easy to establish; the way she broke it off, and then acted “ill at ease” the next time she saw you, are classic signs of someone who does not have a mature outlook.
In this scenario, the next time she saw you she had grown up a little, her standards may have changed, and she realized that you were decent guy after all. Now she wants what you offered before.

2 - The pessimistic (some would say realistic) scenario. She is a narcissist who needs her ego stroked, and has latched onto you for that reason. Let me repeat what guava, since it very neatly describes this situation:

Frankly, I think all signs point to scenario 2. People almost never undergo complete character overhauls in just one year; if she wasn’t that interested in you then, it’s unlikely anything major has happened in just a year to change that. You obviously find her attractive, and she has already been “fishing for compliments about her looks.” Like guava, I have experience with this type of woman (although the one I mentioned in that other thread wasn’t one of them). Don’t think that being a nice guy will count for much when they find someone “better.”
There’s really no way to be positive unless you make a move though. So go ahead. But be honest with yourself: this woman has already spurned you once. You owe her nothing. Don’t go putting your heart out there on a silver platter just for her to carve up.

Im another who agrees with Lizard. Chances are she’s found herself alone, and has picked you out as someone who was keen on her before and will therefore be highly likely to jump through any hoops she decides to hold for you. This has ‘game’ written all over it. Scrap that, it has ‘stopgap’ written all over it!

I hope Im wrong, but tread carefully my friend, and be VERY sure before you invest too much emotionally into this relationship.

Rocketeer is of course correct – it was a Jamaican crustacean. I must’ve conflated him with Rene Auberjonois’ French chef.

It was a French light fixture. Different movie though.

I’d say the more cynical among you are absolutely correct. It feels like Angela wants to see if I’m going to take charge and step up to the plate. There might be some games involved, which is fine by me, as I could use a good challenge right now.

I’m no longer in the business of handing my heart out for just anybody to break – it was already begged for and then ripped to shreds by the last woman I was with. ('Twas a sorrowful story of how insecurity coupled with an inflexible personal narrative became a self-fulfilling prophecy. Stupid sexy writers.) So that “placeholder” quality you allude to actually goes both ways right now – I’m just looking for some entertaining companionship while my heart grows back, and Angela seems as good as candidate as any. But if it’s more effortful than entertainment, fuggedabowdit.

And your (especially Lizard’s) cold reading of her is most freaky given last night’s amusing conversation. We discussed plans for the weekend, and after calling me on my not-as-busy-as-implied schedule, she suggested we make them “tentative”. I said nothing doing, you wanna break a date with me, you need a note from your doctor. She joked (or not), “That works, but if one of us meets someone more interesting between then and now, don’t feel obligated.”

At which point I laid down the law: “Quit it. Friday, I’m going to take you at face value, take you out for a good time, and you’ll just have to accept the consequences.”

“What consequences?”

“That’s for me to know and you to find out.”

Magickly Delicious said it best.

Stop overanalyzing. This is an emotional issue, not an intellectual one. You’re a very smart guy but the answer is in your heart, not your head.

It seems obvious to me you want to sleep with her, that the occasional dinner and stimulating conversation is not enough.

[harsh]
Make a move, for chrissakes. Maybe she wants a little less Freud and a little more Tarzan.
[/harsh]

OK, we crossed posts, but that sounds like a good plan.
Please consider my advice, worth twice what you paid for it.

Er, For you to know, and all of us ten thousand dopers to find out.:smiley: Keep us informed.

I had to laugh when I read this. That woman has incredible nerve (or gall, depending on your point of view). Not only is she trying to use you, but she is trying to get your implicit okay for her to dump you at the first convenient opportunity! Obviously, she doesn’t think YOU will be the one to meet “someone more interesting”!
Un-be-liev-able. Of course, poetic justice would be Saxman actually meeting “someone more interesting” and ditching this self-centered bitch post-haste.

Even so, Saxman, keep up the possessivness bit. That should force her to show her true colors in short order.

Word, Lizard. To paraphrase myself: “Decisions are for adults, waffles are for breakfast.”

If Angela and I end up using each other, it’ll definitely be a mutually beneficial exploitation. I know there are more interesting ladies out there. But as I’m currently focusing on shifting careers, as well as rebounding from a dauntingly unreplicable love, I have no emotional energy left to look for those worthwhile women right now. That said, I may certainly stumble across them – just as I met my current ex-gf fifteen minutes after Angela left that autumn cocktail party.

<faux misogynist>

And as a community service, here’s some advice for any guy finding himself similarly stricken by indecision as I was yesterday:

Quit complaining about dates where the woman “doesn’t know” it’s a date. OF COURSE she knows it’s a date. She just wants you thinking she’s in the dark so she can maintain plausible deniability if you don’t impress her. Screw that. All that matter is that you know it’s a date. Her “cluelessness” becomes moot once you kiss her. Then she has to put up or shut up. (And if she’s a real go-getter, make that “put out or shut up”.)

</faux misogynist>

She wasn’t wearing pyjama pants, now, was she?
:wink:

Terminus, I’m not sure what you’re referring to, so either I’m reading too much into it, you know me in real life, or…

…YOU’RE INSIDE MY F**KING MIND!