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Another awkward first date thread (success!)

ChopperDaveChopperDave Registered User regular
edited April 2008 in Help / Advice Forum
Spoilered for wall-of-text-written-because-I-think-too-much:
There's this girl who floats on the periphery of my friend group who I've had a small crush on for two-odd years. Nothing debilitating, just one of those things where both of us could tell there was an attraction, but one of us was always dating someone else so we just flirted a little bit with the mutual understanding that nothing would come of it. We're remained friends and see each other all the time, but we're not too close and don't know each other THAT well.

We both ended up single a few months ago, and even though our recourse was obvious, for some reason we both just froze. I found that my small crush on her was a lot bigger than I thought it was, and we both seemed to realize that we're actually super shy and awkward around each other when we're both available. I'm not normally nervous about the dating thing, but I really like this girl on pretty much every level and don't want to risk losing her as a friend over this. That's the reasoning that was fueling my pussyfooting until about a week ago, when I finally summoned the cajones to just go ahead and ask her out. She agreed (!), and suggested we go on a honest-to-goodness first date Monday night.

Here's the situation: I've never really transferred out of a friendship and into a relationship before. The one time I tried, well, it ended badly and I'm still dealing with the baggage from it. I honestly don't know what I should be doing on this kind of date, as it's a completely different beast than the sort of first dates where you're just trying to get to know each other from scratch, and don't stand to lose a friendship to the "awkward drift" if things fail to work out.

Like I've indicated, this girl is both capable of being very shy and very flirty. Right now, she's being very shy (but has been warming up again since I asked her out) - probably because she likes me but isn't sure if I'm her type. She's certainly not leaping into my arms and is pretty insistent on going on a date first (rather than the normal college hook up, date later mentality), which is kind of putting me at a loss as to what to do. She suggested dinner or coffee, but both options seem kind of impersonal and inappropriate, seeing as we've already been regularly seeing each other at lunch/dinner and hanging out after classes and running into each other at parties for the last two years. She's still 20, so anything alcohol related is out - not that this would be a good place to start anyway. And honestly, I want to do something interesting, because this girl is really quite pretty and gets asked out by a lot of guys, and I feel I need to distinguish myself a bit.

I know she likes me - she doesn't get this shy with most guys, nor will she agree to a date with many of them - and that I'm already halfway there. I just need a good way to rebreak the ice and get her comfortable with the idea of being more than a friend; I know I can't come on too strong (it would make her uncomfortable), but I can't be weak and forgettable either. I think I need to be convincing, if that's the right word for it, and I'm afraid that I'll get the dreaded "let's just stay friends" after an innocuous and lackluster coffee/dinner date. Anything more interesting and fun that we could do? Any tips on how I can chip away at her shyness and get a second date (at the very least :P) out of her? Am I thinking too much about this?

tl;dr: Asked out a girl who's long been a friend of mine, and while things look promising she's locked herself behind a wall of bashfulness and seems to be sizing me up for chemistry. We don't know each other THAT well, but well enough that a coffee/dinner date would be a a boring and silly place to start. Any other casual date ideas that I can use to show her a good time and break the ice?

3DS code: 3007-8077-4055
ChopperDave on

Posts

  • JustPlainPavekJustPlainPavek Registered User
    edited March 2008
    Bah, I lost an earlier reply so this is a little briefer — I don't know where you're at to offer any specific recommendations, but one of my first dates was a nice afternoon walk through the city arboretum, which then detoured (largely unplanned) to dinner at a nearby Vietnamese restaurant. It was very casual and we were able to enjoy each other's company for several hours, which is all I could hope for. Having the walking-about-out-of-doors to occupy you also reduces the potential awkwardness that might come up sitting across from each other in a cafe situation should you become stalled for conversation, while still allowing the two of you to focus on each other. (edit - I should note that it probably doesn't work if the weather is crap or you both don't actually enjoying walking around in parks, though.) Cooking a meal together is also intimate but maybe a little too much so for a "first date", I don't know. What kind of things does she enjoy doing? What kind of things have you done together in the past?

  • ChopperDaveChopperDave Registered User regular
    edited March 2008
    It's really one of those things where we have the same group of friends, so we end up seeing each other and talking a lot, but only in the context where we're both shooting the shit or eating a meal with at least 2 or 3 other mutual friends. I write and play music and she acts, so we both see and support each other when we have performances.

    The amount of 1 on 1 time we've had is actually pretty low, though I've enjoyed myself a lot when we have done things together (unfortunately, usually just more shooting the shit or going to parties :P).

    The problem I'm having is that she wants a date and will probably be expecting a shift in the tone of our interactions, and I know that this'll lead to awkwardness if I don't handle it right. I figure that I need something that's casual and will get us both to loosen up a bit and have a good time, and I don't think that your standard coffee/dinner first date will help with that at all. But I can't start with something too intimate, like cooking a meal together, either. Feel like I'm walking a bit of a tightrope.

    3DS code: 3007-8077-4055
  • JustPlainPavekJustPlainPavek Registered User
    edited March 2008
    Gotcha. Well, I don't know if I can offer much advice because I haven't gone on that many formal dates, myself. My (limited) experience with girlfriends has mostly come out of situations like yours, though, and I don't think you want to psych yourself out over this. I think just getting out away from the rest of your mutual friends, doing something together and making it clear that you want to be spending time with just her, will start to shift the relationship tone between you naturally. The significance of a date derives less from what you do on it and more in communicating that you want to spend that time focusing exclusively on doing something with her. If the mutual attraction is there — and it sounds like it is, she said yes to this after all — then things will build from there. Sorry I can't think of anything more specific, but it sounds like you're both wanting to give this a shot so don't worry too much over impressing her and just enjoy being together.

  • RegrettableRegrettable Registered User
    edited March 2008
    Going to the zoo maybe? It's a good place to walk around and chat for a few hours and if the conversation falters at any point there's all sorts of cute animals to be distracted by.

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  • UnderdogUnderdog Registered User regular
    edited March 2008
    Going to the zoo maybe? It's a good place to walk around and chat for a few hours and if the conversation falters at any point there's all sorts of cute animals to be distracted by.

    I always hated the zoo because of the pervasive smell of poop EVERYWHERE. But it could work if neither of you are bothered by it.

    I've always liked coffee so it's bad that you already seemed to shoot it down. Coffee is nice. Sit down, relax, and get to know each other. Talk about stuff. Unimportant stuff. Important stuff. Stupid stuff. Smart stuff. Just talk. Then go for a walk if it's nice out. Maybe since you're both pretty well acquainted already, try to do something small to let her know y'know, ya like her. Hold her hand as you walk? What the hell, I don't fucking know, I've never gotten this far (sad, I know). But coffee is always good because you get to talk and connect.

    NO MOVIES! Sit in silence for 2 hours is not a good way to get to know someone.

  • QuillbladeQuillblade Registered User
    edited March 2008
    I am not too familiar with how the process goes from casual friends to something deeper- it seems to be a thing which is different for everyone. The spirit changes, and such a thing is often held in tiny unexpected details. I see that you see each other often, and there is mention that this be a more formal setting, maybe to help make distinguishings between your casual friendship and the new style of relationship?

    You seem concerned more about procedure than you are worried about what to feel, which is good, if you both feel the same way, you will get closer through anything you can both enjoy together. Relax and know that this is the way of it. Spend time, enjoy being yourself and yourself with her, and she will enjoy your company too. But back to the formal part.

    You should get her at least one flower. That is a formal rule of a formal date. A signal that it is date time now, not friends time (although in truth it should always be both, right?). You need to sit down somewhere and eat a meal alone together. You should always compliment her dress, and then you need to find a flower in your heart to give to her to match. What I mean is, look at her style, her presence or spirit of character and find something specific about it you enjoy and tell her. This is your gift, and will not be forthcoming without some small fear- but that is the gift, the first step in trust with your emotions. This is a sign, a signal, that you are and want to be emotionally connected.

    Then after talking, you should share something sweet together. Not in two dishes, but share something at the end. The exact same thing. This is another formal signal, that you are wanting to be in step, in sync with her life in this moment. In a delicious, enjoyable moment. In this way, you establish that your desire is to be united moving forward, delighting in a positive situation- and that is the very start of a relationship.

    Three simple signs. But I think important for you because you are changing the definition of something previously established and there is a desire on both sides to be clear. So find these signs. Use them to mark your way. It seems from your post that both you and she desire this.

    Owl cocked his head and asked,"What should I inquire about?"
    Raven said, "Good start".
  • OremLKOremLK Registered User regular
    edited March 2008
    Along the lines of the zoo, but without the aforementioned pervasive smell of shit, why not a museum? An art museum so it's not so nerdy, perhaps? Just a thought. I like the arboretum-before-dinner idea too.

  • SarcastroSarcastro Registered User regular
    edited March 2008
    I wouldn't be so quick to toss out dinner at a nice restaurant. It seems cliche, true, but its more about the execution, the details, rather than the basic idea.

    Besides, sounds like you're looking for an excuse to spend some quality one on one talk time. Dinner is a good start on that.

    If shes into it, art galleries can be pretty decent, as can shopping for something at a large mall. Say you're looking or a shirt or something. Then get one. Spring for lunch while you're there, and then if things are going well, dinner after. See Also: dont forget the frangrance section at the Bay (or US equiv.) Find a scent she really likes on you and I tell you what, half your battles are fought already.

    Edcrab wrote: »
    "See," said Lucifer, "God's an asshole."
  • duonguyenduonguyen Registered User
    edited March 2008
    So you two have been in the same group of friends for a while. It's your chance to impress her. You say she has a lot of guys after her, you don't want to do the same normal thing, do something special. Look or search for special event happening around your area. It doesn't have to be anything too romantic. Just an evirroment where there's somethign happening and you don't always have awkwards silences. Think of this date as you are trying to entertain her doing something that will be a first for you and her, that way you'll get more dates out of it. Some place that will offer chances to flirt too or initiate contact. And then taking her to a good palce to eat, no expensive but someplace cool, and good dessert. And pay for everything damnit! that shows that you are interested in her more than just as friends.

    For examples (from my own exp.): Science centers, just joy riding around town (good music is key), parks/gardens, amusement parks, since you guys are both interested in the arts, maybe hopping in one of those dance classes one time.

    Edit: Sarc has some good ideas, as in going palces to get something to done (buy items), but on a date you don't want to make it seem like she's just tagging along to help you pick soemthing out. Make it seem more spontaneous.

  • seasleepyseasleepy Registered User regular
    edited March 2008
    Museums, art galleries, nature trails, shopping, etc -- those are the sorts of things you want to be looking for. Stuff where the two of you can chat and wander while looking at stuff. Go and get a coffee afterwards (or a meal, depending on the time) and keep talking. All you really need is to be able to hang out, together, alone.

    Whatever you end up doing, since you're both nervous, I wouldn't make it a big production, and try not to over-plan it. It's a first date, and first dates are important and all that, but if you do something you can both have fun with, enjoy each other's company, and go with the flow of the day/evening/whatever, you should be fine.

    It was amusing to have Massachusetts as part of our country, but now, of course, like so much of the coastal nation, it no longer qualifies as America.
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  • ScrubletScrublet Registered User regular
    edited March 2008
    My (limited) experience with girlfriends has mostly come out of situations like yours, though, and I don't think you want to psych yourself out over this.

    Key. Don't psych yourself out. The second you start putting this girl up on a pedastal, and start worrying about how you can fuck this up, you already have. Relax! I would go with any of the aforementioned ideas in the afternoon that get you doing stuff together ALONE. Then if it's natural, transition into dinner.

    Another note, since you have multiple mutual friends: try to avoid frequent mutual contact with the two of you and your friends. Everyone will be used to everyone being friends, and that dynamic is contagious. Establish the fact that you two are more than that, then start doing shit with everyone else.

    subedii wrote: »
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  • ChopperDaveChopperDave Registered User regular
    edited April 2008
    So I thought I'd go ahead and give a follow-up to the thread, for those of you who enjoy hearing the results of these things:

    We ended up postponing the date til tonight, and thankfully it wasn't an elaborate April Fool's Day ploy on her part. Drawing here and there from the advice of everyone, I did NOT go to the zoo (hah), but instead took her shopping at the Salvation Army and then to dinner. One fly tweed jacket, a shared sushi boat, and plenty of awkward/silly conversation later - doing my best not to psych myself out, I swear - I got a 20-minute goodnight kiss (:winky:) and a second date set for later this week. Hi5!

    Seems like things are looking up. I think the plan is to do desert/coffee at a place that will have a special jazz show that night, and then if things go well from there I might attempt the cooking thing Pavek suggested for the third. Maybe that'll be an appropriate time to get a flower like Quill suggested, who knows. Anyway, thanks for the advice everyone! See you at the break-up thread :P

    3DS code: 3007-8077-4055
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