Why isn't this working?

September 22, 2008 6:27 AM

I've tied myself into a knot trying to date someone and need to undo it.

A woman and I have been getting together, having dinners and such regularly for about two weeks. I really thought we had a lot of things going for each other. I'm rather shy and slow to initiate physical contact. Now, I can't tell if I just missed the boat (in which case maybe I should try to catch it at the next stop?), or if this just isn't supposed to happen.

Further information that would help in considering this situation: we have a lot of common interests and laugh a lot when we get together. Overall, she's been enthusiastic about hanging out. I look for flirtatious signs when I see her but don't see a lot. I probably fucked up on the first date by saying goodbye and turning around without so much as a hug. Now, I sometimes feel a tension in our conversations - she is a sparkplug type (which I like), and I fear my own directionlessness with this whole thing has even frustrated her a tad. I know that one answer is to just up and kiss her, but somehow I feel conflicted, as if she perhaps wouldn't appreciate it, and that to do so would be ignoring counter-signs worth listening to (periodic awkward pauses, odd disagreements over rather random mundane issues of politics and taste, sort of a staunch refusal on her part to send physical signals or even be up for something like a drink to loosen things up). So, maybe I can hit bottom at this by saying: I know the advice, at some level, is to get in touch with the gut and follow it. But how to step back and get in touch with the gut in a situation where I feel like I've tied it and a bunch of bullshit together into one big, gnarly knot?

Final tidbits before handing this over to the hive:
--She's from out of town and doesn't seem to be immediately loving the new environs...things are in general a little topsy-turvy for her
--I can be pretty cerebral but in general have a fairly healthy social life + other interests (music, biking, etc)
--Our conversations have been very wide-ranging but haven't stepped much at all into what our personal lives are like/have been like (though I am at least nearly 100% certain she is unattached)
--This has happened to me before, more than once. In the past, I've let this kind of thing go on for months until it drives me up the wall and I bring it up in a way that is way too little, too late, and very unproductive.
--I think overall I don't have 'attractiveness' issues and really want to get past this trend I perceive where my most successful relations with women rely on the woman for an uncommon proportion of the relationship-initiation work.

posted by LoneWolfMcQuade to human relations (22 answers total)

Be direct and talk to her. "I really like you but I'm not sure if you feel the same way. I know this is an awkward way to approach this, but I'm afraid that I'd me missing out on something really great if I didn't."

Direct communication works.
posted by DWRoelands at 6:45 AM on September 22, 2008 [7 favorites]

Seconding DWRoelands. It's hard to take the first step, but it's much easier to deal with than the circles you're running in. If she feels the same, that's wonderful. If she doesn't, well, that's too bad, but at least you know where you stand.
posted by mitzyjalapeno at 6:49 AM on September 22, 2008

I think the key with working your way up the ladder of physical encounter is to start at the first rung of that ladder. If a kiss is halfway up the ladder, and you just jump for it, you are more likely to crash and burn. So, start initiating much smaller and socially acceptable forms of physical contact. Touch her arm during a conversation, etc. Start with physical contact that you would feel comfortable doing with any friend and don't take the next step up the ladder until you are comfortable. I am convinced the reason why first kisses can and do sometimes fail is that its too dramatic of a transition. "Wow, we are having a great conversation and OMG WHY IS HE TRYING TO KISS ME!" Instead, take the baby steps in terms of physical contact that make a kiss seem much less intimidating and suspiring for either party involved, plus you will be able to tell very early on if she is open and reciprocal to physical contact with you that will allow you to disengage and save face if necessary.

I think the key is avoiding the big leaps up the ladder, which are more likely to make both of you uncomfortable.
posted by jlowen at 6:52 AM on September 22, 2008

I know that one answer is to just up and kiss her, but somehow I feel conflicted, as if she perhaps wouldn't appreciate it, and that to do so would be ignoring counter-signs worth listening to

Is she an old friend, or someone you work with, or someone you will otherwise have to see and interact with for years to come?

If not, there isn't much to lose by making a move. Worst case is she gets angry, tells you she's not into you in that way, and both of you move on.

My point is that seeking clarification (through your actions, not words, usually) is a good thing, even if the answer is negative. Even if she says no, you are then free to put all this romantic energy into the next woman, and the one after that, rather than remaining stuck in dating purgatory forever with this one.

I used to be very like you, deeply afraid to take a step forward in case the results were embarrassing or she was insulted or something. But there was a very specific day, shortly after a long relationship had ended, that I decided to approach things differently and just not give a shit about rejection. It was honestly that simple — I thought about it, realized that my current approach to dating wasn't working well, and that instead I needed to behave differently.

The irony of it was that being willing to risk rejection turned out to mean that there was a lot less rejection, because being willing to step up and take a few risks turns out to be a lot more attractive than your current approach is.

So I can't give you a step-by-step from where you are to where you want to be, other than to say that I made a similar transformation very easily, once I decided that it was important to me. I think it was so easy because it's small things, really, and things that your gut is already telling you to do, like holding her hand or kissing her or asking her out.

I think the answer to this:

But how to step back and get in touch with the gut in a situation where I feel like I've tied it and a bunch of bullshit together into one big, gnarly knot?

is to acknowledge that the problem is a lot simpler than you are making it out to be. You think she's cute and would like to take the romance further, and you need to know if that feeling is mutual. Sounds reasonably accurate? In that case, you can talk with her about it, you can do things like briefly hold her hand during dinner and see how she reacts, or you can snuggle your face right in next to hers while talking at the loud bar, just to pick some random examples. If she reciprocates — smiles, holds your hand, rests her cheek against yours — you continue; if she doesn't, you have a pretty big hint about where her feelings lie.

And I know that doing so the first time takes guts, but a really good way to clarify what is going on and how she feels is to say (directly, without any caveats or self-deprecation): "Hey, I've really been enjoying hanging out with you, and I wanted to ask you out on a real date to do [activity] on [day and time]." That way you acknowledge the ambiguity of what you two have been doing, and clarify your intentions that the next time you get together will be a date with romantic intentions. It's tough to say the first time, but after that it's really easy, honest.
posted by Forktine at 6:57 AM on September 22, 2008 [3 favorites]

You could ask if she'd like it if you kissed her. That's what Mr. Sidhedevil did, and it worked for me.

There are women (I'm one of them) who resolutely avoid being flirty. Thus a more direct approach is required. If this lady is an anti-flirt, then the "put your hand on her arm" and what-not may not actually yield the results you're looking for--I know that in my dating years, any groovy suave Casanova moves from my date generally pushed me further into jolly-hockey-sticks territory.
posted by Sidhedevil at 7:07 AM on September 22, 2008

My point is that seeking clarification (through your actions, not words, usually) is a good thing, even if the answer is negative. Even if she says no, you are then free to put all this romantic energy into the next woman, and the one after that, rather than remaining stuck in dating purgatory forever with this one.

My response here would be distilled into that comment by Forktine. It's time to find out if you're in dating purgatory or not... I've been there and at least once it was up to me to extricate myself.
posted by crapmatic at 7:17 AM on September 22, 2008

Oh man do I feel you. It's difficult to be expressive or get the girl to be comfortable enough to initiate conversations or whatever else. Despite your sincerity, she will still be frustrated by your hestitance and/or tendency to step on her toes during the dance. It may be that you are unequally yoked in affection. If your anything like me, you should express through your actions to give her avenues of (verbal) approach.

For an example, I can write like a lyricist but speak like a child, I prefer not to say too much; which was a bit unsettling for my woman of interest. Last night, at her going away gathering, she preferred to give her attention to the other fellas because I just wasn't hitting my points. Until towards the end when I presented her her only gift with a note which brought her to tears. I expressed myself in a manner that is most effective for me. Darts sent truly from the heart. Be true and real (TRILL) and anything that happens you will be comfortable with.
posted by Student of Man at 7:24 AM on September 22, 2008

I am this guy, whose issue was how to go slow without missing the same boat you're talking about. So it's not 100% the same issue as yours but similar. I say go for a hug next time and then next time a hug and quick kiss on the cheek. See how those go down and you'll then be in good position for a smacker if other indicators have pointed that way. The point is to indicate some interest while staying somewhat true to your slower ways. And meanwhile let your gazes, words, laughs, emails, and actions indicate your interest. What a difference a week can make, I found in my case. I wanted to go slow and not rush things but not fizzle, but things kind of sped up a bit unexpectedly and are looking great. Cerebral types like us can certainly spend a lot of time analyzing it, but we kind of forget that things are going to take a course that is only partly in our control, and that we can't predict everything. So, patience sucks, but pays off, as does relaxing. Also, these perceived faux pas are rarely as big a deal as they seem once they echo around our heads 1,000 times. She's aware of early-date awkwardness, so you can recover. Good luck!
posted by Barbecue at 7:25 AM on September 22, 2008

Love is chemistry. Either it's fusion or combustion and little else except inertia in between. So, the question is - are all the elements in their rightful place? Is the timing right? Are you both on the same wave length? And most of all - is this even plausible. The only way to know for sure - is to straight out communicate with her. Speak. Ask. Investigate. Journey with her and speak what it is your heart - from your heart.
posted by watercarrier at 7:53 AM on September 22, 2008

odd disagreements over rather random mundane issues of politics and taste, sort of a staunch refusal on her part to send physical signals or even be up for something like a drink to loosen things up

Dude. It's not going to happen.

You don't really click with this woman either ideologically or physically. If she is not willing to loosen up, to allow herself to feel comfortable, allow her guard down around you, then that's a big red flag right there.

Yeah, there is the chance that this may lead to some physical relationship - but only if she feels she needs it - i.e. she is on the rebound, or "it's been a while, why not?" It doesn't sound like that is going to happen. You need to move on.

Stop focusing on this one woman. You gave it a good try, and it didn't pan out. IT'S NOT YOUR FAULT. You didn't do anything wrong, you're note defective, or unattractive - she just simply isn't right for you.

Get out there and meet someone else - preferably someone who isn't such a cold fish. And let this be a lesson - next time you're seeing someone like this (and there will be other women like this, I promise) don't over think it, or rationalize it. If it doesn't feel right, it probably isn't right.
posted by wfrgms at 8:14 AM on September 22, 2008 [1 favorite]

I can't help you with the contraindications, but as for the what-to-do, listen to jlowen and Forktine about the ladder. The two keys here are the circumstances and slowly working up to things. So, first, maneuver yourself into darkly-lit situations or situations where you spend extended time alone, ideally side to side (eg, go out to a movie, or cook for her at your house and then rent a movie, or look at photo albums or comic books). Then, just try to generally get closer to her from the side. By the time she's leaning up against you, you can be sure it'd make sense to hold her hand or put your arm around her so she'd be more comfortable. If you see her trying to deescalate either the circumstances ("no, let's go to a party with eight people instead") or the closeness, you should probably back off.

Also, you may not need to carry all this pressure and angst. I'd say that most of my relationships went through an awkward period like this. You don't have to feel like it's your fault or responsibility (she can suggest things, too).
posted by salvia at 8:18 AM on September 22, 2008

I don't think trying to maneuver this situation into a SURPRISE! PHYSICAL INTIMACY! kind of place is a good idea. It sounds like you've made a friend, and she doesn't sound like she's looking for the same things out of your relationship as you are. Asking directly might be a better plan.
posted by nasreddin at 8:43 AM on September 22, 2008

You can try to kiss her, and fuck it up, or *Not* try to kiss her, and it fades out and fucks up anyway.

Looks like you ought to just fucking kiss her. One way to take the edge off things is to ask, "Could I, like kiss you?"
posted by notsnot at 9:08 AM on September 22, 2008

If she is not willing to loosen up, to allow herself to feel comfortable, allow her guard down around you, then that's a big red flag right there. ... Get out there and meet someone else - preferably someone who isn't such a cold fish.

In a private message another user pointed out that these statement sounded kind of jerky. Please allow me to qualify:

What I mean is that if this woman is physically resistant to your well intentioned, non-creepy overtures, and doesn't initiate physical contact on her own... then that's a sign that the chemistry just isn't right.

I didn't mean to imply that she should "put out or get out" - just that she's not that into you.
posted by wfrgms at 9:33 AM on September 22, 2008

DWRoelands: "Direct communication works."

To present an alternative viewpoint on this one, direct communication can often not work, too. It can be misread as intensity or getting too serious too quickly — even if it is specifically not phrased that way.
posted by WCityMike at 9:44 AM on September 22, 2008

What I mean is that if this woman is physically resistant to your well intentioned, non-creepy overtures, and doesn't initiate physical contact on her own... then that's a sign that the chemistry just isn't right.

Not necessarily. It might mean that she's shy or reserved or just resistant to physical flirting. I know it has in my case, even when I was really into the guy. There are some women who are very very ambivalent about the culturally-approved stereotypical ways that women are expected to behave.
posted by Sidhedevil at 9:51 AM on September 22, 2008

Thanks everybody, it's amazing to me how quickly and effectively a question like this can receive insightful comments.

I'll start with my initial assessment, which is, across all of the comments, there is a theme to think less, simplify, get in touch with internal emotions, and let that dictate next actions, which are probably best taken with continued patience in baby steps. I agree with those such as Forktine that fear of rejection is a dragon one is best off slaying as quickly and directly as possible.

In this case, however, I think everyone's feedback has pushed me to a bit of a self-confession: knowing what I know, and taking a little more time to look inside and see what's there, I think there isn't much more conversation to have with this individual, at least in trying to move in the romantic direction. Looking back at our past conversations, so many of the roads I know to intimacy have been peeked at from over the hedge, with no real ensuing spark of chemistry, or encouragement to move forward. And even if that wasn't an inevitable outcome, maybe it's okay to accept it as the outcome in this case.

I appreciate people's comments for me not to worry or blame myself - I'm going to take those to heart, while also keeping in mind people's calls for one to be as forthright as possible with others. So, maybe the next step for me is to hang out with her holding no expectations, take a quick gut check, and unless there is a surprising change in the tone of our relationship, just consider things to be on a solid friendship basis.

Finally, as if all this reflection weren't enough, I'll post the notes I took on the comments - I figure it might be a useful summary for people who are interested in this question, and as possible fuel for any further comments that can build on what's already here.

Thanks again!

Counts of suggestions (some people made more than one suggestion in their posts, so there are more suggestions than posts):

be direct and talk about it - X X X X X
move carefully up a 'ladder' of physical contact - X X X X
one way or another, embrace the possibility of rejection - X X
forget expectations of outcomes and do what feelings dictate - X X
patience, recovery may be around the corner! - X X
not gonna happen, kid, not your fault, and just take it as a lesson - X X
just (*&^#ing kiss her! - X


Other points:
1. Some women aren't very flirtatious, which casts doubt on the whole 'ladder' approach (or at least its universality) (Sidhedevil);
2. One may fear rejection, but delving head-on toward its possibility can be liberating (forktine, crapmatic);
3. Be patient through lack of recognition and let your action have its own effect (Student of Man);
4. If you're extra-cerebral, it's just that much harder to pass through an extended period of awkwardness, one that may not actually indicate any problems at all (Barbecue);
5. High uncertainty is another way of being told 'no,' or at least, 'this doesn't work.' (wfrgms)
posted by LoneWolfMcQuade at 9:57 AM on September 22, 2008 [4 favorites]

Put me in with the just %^&*inf kiss her already crowd ... but heres how I overcome The Fear (tm) to make it happen.

At that point, I think of the Me Of Tomorrow - how annoyed will I be tomorrow that I didn't make a move, at least hold hands, or touch her shoulder or kiss her or SOMETHING...

Also, what have you got to loose? You go to hold her hands, or kiss her, she's not interested in you that way ... and you are where you are now, except you know where you stand. Its a win win situation, you win twice!
posted by Admira at 2:58 PM on September 22, 2008 [1 favorite]

knowing what I know, and taking a little more time to look inside and see what's there, I think there isn't much more conversation to have with this individual, at least in trying to move in the romantic direction. Looking back at our past conversations, so many of the roads I know to intimacy have been peeked at from over the hedge, with no real ensuing spark of chemistry, or encouragement to move forward. And even if that wasn't an inevitable outcome, maybe it's okay to accept it as the outcome in this case.

With all due respect, what you are doing here is just a continuation of your initial inability to make a move. You have decided, on your own and from a distance, that there isn't "encouragement to move forward." While that might be true (I think it's very likely that she found a friend, while you were looking for love), the whole point of what many of us are saying is that you need to stop doing all this in your head, and have the courtesy to ask her how she feels.

You can do this verbally: "Hey, I'm really liking you, how do you feel about a kiss?" Or you can do it physically, by flirting with touch and looking for reciprocity. Or you can find some other way that works for you and works for her.

But whatever method you chose, you need to start thinking of "making a move" (that is, assessing whether the interest you feel is actually mutual) not as an imposition and a risk, but rather as a kindness and an act of polite clarification.

Doing so prevents social awkwardness, and prevents those ghastly situations where one person pretends to just be interested in friendship, and the other person is correctly horrified when the pent-up frustration of a decade-long crush is dumped out one drunken night.

Again, you are making this complicated, when really it's pretty simple. Do you think she is cute and fun and nice? Then ask her on a date-with-a-capital-D or hold her hand or whatever. Then, and only then, do you need to deal with the "what next?" question — what if she laughs at you? what if she marries you but turns out to still miss her lesbian ex? what if she arranges for you to be probed by space aliens on a deserted road in Nevada?

Those are complications for later, not for the present. For now, it is honestly (really, it is) as simple as do you kind of like her, maybe enough to want to kiss her? If so, make a move. If not, move on and ask some other woman out this weekend. Doing anything else is just doing more of what isn't working for you. You have correctly seen that you need to make a change, but the only way to do that is to, well, do that.
posted by Forktine at 4:13 PM on September 22, 2008

If you can't do this for yourself, do it for her. Regardless of what signals you THINK she's sending, for all you know she could be posting a question in a parallel AskMe universe asking why you won't make a move. Some women *cough cough* torture themselves for days/weeks/months wondering why he didn't ask her out/call/kiss. Human beings mostly suck at reading each other's romantic intentions, and some human beings tie themselves in "big gnarly knots" over it.

SPARE HER THE AGONY.
posted by desjardins at 5:38 PM on September 22, 2008

Hey, I love the little analysis & summary of the thread! I wish more people would do that.

Gotta say, I can't hope to keep up with the relentless clarity of Forktine's comments, so here's a bit of a grab-bag of mostly unrelated thoughts that I don't think have been covered yet:

You say she has a "sort of a staunch refusal on her part to send physical signals or even be up for something like a drink to loosen things up". This sounds very unpromising, but do you know if there's anything in her background (eg a strict religious upbringing) that might explain this? Just speculating.

No mention of private lives, in a couple of weeks of conversation? Interesting. A woman with a partner, in ambiguous date-like situations like that would usually slip in a "Hey, what a coincidence - my SO & I were just talking about that the other day!" or something along those lines just to clarify her status. Less frequently, a single person might drop a reference or two to "my ex". No mention of those things at all sounds a bit like demarcated territory - ie "sorry, none of your business".

Somewhat alarming that you don't sound like you've broken any physical barrier yet. Do opposite-sex friends where you live not give each other hugs and / or pecks on the cheek or lips when they meet & depart from each other? Just wondering, because a fair amount of meaning, one way or the other, can be communicated through quite subtle differences in that act.

Finally, seconding what I think wfrgms was trying to say about chemistry - she may be cute & interesting, but if you're not feeling a whole lot of warmth coming from her, let alone a mutual spark, is that really the person you want to be in a relationship with?
posted by UbuRoivas at 7:33 PM on September 22, 2008

She's from out of town and doesn't seem to be immediately loving the new environs...things are in general a little topsy-turvy for her

Overall, she's been enthusiastic about hanging out.

Is it possible she likes hanging out with you because she's new in town and doesn't know anyone else? I.e., her agenda may be one of meeting her own needs (for human contact). This is a different situation from the usual one, in which people who like hanging out both have the agenda of seeing whether a relationship can develop.
posted by exphysicist345 at 8:01 PM on September 22, 2008