Possible Dating Dilemma Approaching…

The first date on Thursday night with Twinkly-Eyed Guy went well. Very well. [Can you hear the ‘but’, yet?]

We had dinner together by the Opera House, overlooking Circular Quay, and chatted easily. Then we saw ‘The Informant!’ – excellent film with an outstanding performance from Matt Damon – and then we got ice-cream and strolled around a while. After which we sat on a bench and watched the enormous cruise liner leave harbour… and then he leaned in and kissed me, gently but pretty confidently.


So, we smooched on the bench for quite some time like a pair of sixteen-year-olds (i.e. awkwardly positioned, not terribly comfortable but persistent as well as surprised that it was actually happening and slightly concerned about how far was too far for a first date) until we called it a night at about quarter to one and I caught a cab home.

It was good, but not earth-shattering. He did everything right, he really did. He has the confidence to know what he wants and make a first move, but he is by no means arrogant or conceited. He’s intelligent, well-travelled, independent, considerate, kind and good-looking.

[Are you sure you can’t hear the ‘but’ yet?]

All of which is good… but…

Remember, the weekend I met Twinkly-Eyed Guy, I also met Tall Pilot Guy?

And you know what a Thing I have for tall men, right? I can’t help it. Even though I know its about me, and my insecurities, not about them. I’m tall, and I simply don’t feel powerfully Amazonian with a shorter guy, I feel like a galumphing great freight truck.

[Hence, sitting on the bench kissing Twinkly-Eyed Guy was okay but standing up kissing him felt odd. Maybe just unfamiliar odd, I know, I know…]

Anyway, the evening I met Tall Pilot Guy I had to leave early to go canyoning the next morning at Oh My God O’clock. So we didn’t swap phone numbers or email addresses – although we did discover that we live on the same street and mentioned which blocks we lived in, just not the actual apartment numbers. And then he apparently asked after me the next day, which floored me.

With impeccable timing, the mutual friend who introduced us went away on holiday so I figured I had no way of contacting him, short of bumping into him on the street in the next couple of weeks before all memory of me faded or sticking a note to the door of his building… and the latter idea was abandoned after a morning’s consideration since it seemed to smack of desperate stalker-ness.

And guess what, we bumped into each other on Saturday morning.

“Hi!”, he said, “I’ve been hoping I’d bump into you again. I keep walking past your building and wondering if I should leave a note on the door, but I thought that might be creepy so I didn’t. How was canyoning?”

He apologised for looking rough as he’d had his work Christmas party the night before – believe me, he did not look rough. Or at least, he may have done, but I liked it. πŸ˜‰

Well, we’ve swapped numbers now, so I really hope he gets in touch and asks me out to something which is obviously a date before Thursday, as opposed to a) not getting in touch at all or b) not getting in touch before Thursday or c) asking me to something which could easily just be a friendly thing and which I would thus be paranoid about misinterpreting.

And why before Thursday? Because that’s when I’m due to go on the second date with Twinkly-Eyed Guy and I don’t want to lead him on when, to be honest, I think at this point I’m more attracted to Tall Pilot Guy.

Everyone should have such problems, yes?

How many dates do you go on before its supposed to be exclusive, anyway?

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26 Responses to Possible Dating Dilemma Approaching…

  1. Pete says:

    I also hope Tall Pilot Guy gets in touch before Thursday. And call me old-fashioned but I think kissing on the first date could be too soon. It certainly was for me in my last relationship. But I’d say get to know them both and then decide.

  2. piereth says:

    Sounds wonderful – a veritable buffet of lovely chaps!

    As to when it goes exclusive, it’s up to you. Dates are, after all, dates. In my own mind I suppose it’s if / when you take your snogging / fumbling onto a more, ahem, visceral plane. Till then, no-one has any exclusivity in my book. Although, I agree about the ‘leading him on ‘ thing. If the fireworks aren’t doing their stuff after the second date with TEG, or you see no chance that they will, step back.

    Is it too soon to kiss on a first date? I don’t think so. At any rate, I’d be a thumping great hypocrite of I did! xxxx

    • woo says:

      ah, so far, just kissing – no fumbling. All quite gentlemanly. But yes, in retrospect I’m not a huge fan of kissing in public, first date or not.

  3. David says:

    An embarrassment of riches, indeed!

    Here’s what I’d say. Give Twinkly Guy a second date; you never know. However, maybe back off on the kissing … not in any rude way, but just with a friendly, “We should probably hold off until we know each other a little better.” His reaction to that will tell you more about him than another ten dates will do. But you don’t want to close that door until you know more about Tall Guy. Initial attraction can be so deceptive … not always, but sometimes.

    You’re not exclusive until you’ve had the specific conversation in which you both commit to being exclusive. C’est tout. Even having sex doesn’t make you exclusive until and unless you both agree it does … which is why it’s so important to have that conversation before things get to that point.

    • woo says:

      we’re off on our second date on Thursday night (to the Moonlight Cinema in Sydney’s Centennial Park) and I do feel that I’d prefer not to do too much of the public kissing there, so I’ll see whether he tries it and take it from there.

      And I think there’s an interesting difference in opinion about the step between ‘dating’ (no exclusive) and ‘going out with’ someone (i.e. being exclusive) which possibly reflects different approaches between the UK and US on dating.

  4. modestypress says:

    Raining and pouring…perhaps you should wear a raincoat, perhaps a rain coat with nothing on underneath.

  5. doctordi says:

    Good grief, Modesty, that’s a trifle, er, immodest to say the least!!!

    Guys, I’d simply *love* to know how Woo is supposed to tactfully back out of kissing TEG next time having already launched into a session of bench petting. Once you’ve got a precedent, and darling, you do, personally I think you’re hard pressed to say, ‘Oh, no thanks, no kissing tonight’ next time round. Imagine the situation reversed. Do you not think you’d race to the toilet to breathe into your hand, and then spend the rest of the night agonising about what went wrong? I sure as hell would, and I’d be surprised if that’s an unusual reaction. Of course, if you don’t want to kiss him, that’s an entirely different matter. Then don’t. One thing – you don’t say he’s funny. I do think for you he would need to be funny – don’t you?

    I hope you hear from TPG before Thursday too. I can’t imagine dating multiple people at once, but I can imagine going on a couple of dates with each suitor and then regretfully declining to go further with one of them. Just see how you go, relax, don’t worry about it. You seem too decent a person to lead anyone down any primrose path even if you were wearing a dodgy raincoat.

    • DDi — I’ve done it in the past by saying: “You know, I had a great time kissing you last week, but in retrospect I think we might have moved a little too fast, and I’d be more comfortable taking a step back.” If someone said that to me, I wouldn’t read any subtext into it; I’d assume that she was telling me she’d made a small error of judgment as far as where she wanted to go and when. I might be an aberration, though. πŸ™‚

      • doctordi says:

        Actually, David, when you put it like that I agree it doesn’t seem so horrifying. A nice little compliment about the previous session might be all that’s required.

    • woo says:

      hmmm, and as I know I am the kind of person who is better at ‘frank’ than ‘gentle’ I’ll have to tread carefully with any kind of backing off messages. But we’ll see how it goes on Thursday night.

      I’m glad you think its okay to go on a couple of dates with each of them before deciding… which is, to begin with, a huge assumption on my part; hoping that Tall Pilot Guy actually asks me out and I get to make that decision. They may both decide to run for the hills!

      • doctordi says:

        Yes, I think that’s totally above board, Woo. There’s a massive difference between a couple of dates and formally going out with someone. On reflection, though, moving in for a big public pash on the first date is making TEG nag ever so slightly… but it’s not a sackable offence so let’s not be too hasty!

  6. Fugitive Pieces says:

    The fastest way to stop the agony? Ring Tall Pilot Guy, now, and ask him out for coffee, asap. Go out on Thursday with Twinkly-Eyed Man, regardless. Start paying attention to what you want, and when, and from whom: you are an enormously polite person, almost reflexively, but you’re not going to break anyone by thinking about yourself as well as them. Slightly more, even?
    I don’t think there are rules, here. You might well need time spent with both, before you choose. (Yes – you! YOU get to choose! Not just be chosen!) Incidentally, I had a friend in almost exactly this position (you’ve met her); she resolutely refused to let guilt or anxiety make her panic until she knew which man she trusted, as well as desired… and she would be the new mother, and engaged to boot. So have faith in your own right to make an informed decision, pet, and do your best to sit with the uncertainty until you’re ready to make it.

  7. woo says:

    Ah, but all this is a result of me not making any real effort when I first met them both, so I am loathe to jinx my luck by changing tack now and pursuing TPG. I will possess my soul in patience and will him to call!!!

    I really appreciate the point about thinking about myself and what I want, though. Absolutely heard and understood. And if it worked for S, then so much the better!

  8. Double ha. Go out with both of them, of course! What is this exclusivity thing you speak of? Until you are seriously involved, by which I mean having great sex and you don’t want to have it with anyone else, you can date, coffee, kiss, play footsie to your hearts content. With as many people as you can fit into your schedule.

    My rule when I was dating was I never kissed anyone unless I was sure I wanted to go to bed with them. This meant that there were a lot of guys who never got kissed at all. But in my humble opinion, kissing is the beginning of foreplay, and once I get well started on foreplay I am not usually of a mind to stop the action. So, no kissing unless I was serious about sex. I’m afraid this personal rule may have given some people the opinion that I was “easy” because once they got to first base they had a potential home run on their hands, so to speak. Other people had the opinion that I was impossible because they couldn’t even get to first base. But that was just my rule.

    I have no idea what the rule is about how many dates before you commit to being exclusive.

    • woo says:

      You know, I think I had pretty much the same rule when I was in my twenties. πŸ˜‰ With pretty much the same results (i.e. a great deal of fun).

      I fully intend to enjoy date #2 tomorrow night…

  9. Pete says:

    I’m going for a third date on Thursday and still no kissing other than the polite peck on the cheek kind. (I feel positively backward in comparison.) I’m trying not to put pressure here but third date is often ‘make or break’.

    Good luck with yours – both with TEG and TPG. I’m interested to hear more about why you prefer TPG. Also interested to find out for myself whether taking time to pause before rushing in makes things better or worse!


    • woo says:

      Well, I think that if a man didn’t at least try to give me a ‘proper’ kiss (by which I mean a kiss that couldn’t just be the kind given to family members) by the third date, I would assume he didn’t find me attractive and was just wanting to be friends… which would be fine, except that you clearly like her more than just friends!

      And as to why I prefer TPG – I’m not sure I know, to be honest. It is definitely partly his height, which makes me feel comfortable about my own height.

      Maybe its just the fact that he seems less available (and, sadly, it seems to be a human trait to value things which take more effort to acquire), or maybe its that his job in the RAAF reminds me of my father, who worked for the RAF for 30 years. (Scary freudian thought)

      But I suspect it also has to do with the fact that – although we’ve only spoken briefly – he gets my sense of humour more than TEG and made me laugh in return, which TEG doesn’t – and that TPG is more outdoorsy, like me, whereas TEG spend a lot of time at gigs and events at night, with work and for pleasure. He’s a night-owl, and I’m not.

      But we’ll see. TPG still hasn’t called, so I guess I won’t get to find out why I like him!

      • Pete says:

        That explains it perfectly. (And damn you, TPG, for your mixed messages!) Maybe TEG will grow on you. And good luck for your date!

  10. piereth says:

    Just me being perverse, possibly – but why not cease to analyse, and enjoy the moment?

    You can’t plan these things, and we all want you to succeed, and we’d look like idiots if our ‘dating by committee’ made things more complex than they really are!


  11. doctordi says:

    Piereth makes a fine point, Woo. Shutting up now – will stick to crossing fingers!

  12. azahar says:

    Well said, Peireth. “Dating by committee” – meh.

    Two guys you like. Lucky you. So now it makes sense to find out how much you like them by finding out more about them. Easy, eh? πŸ˜‰

  13. Deb says:

    Oh darling, my heart is bleeding for you right now. What a dreadful dilemma!

    I’m still a bit astonished that two of my real world friends are blog friends… I was saying to Doctor Di yesterday (over the simply amazing Christmas lunch she cooked us at her splendid Manly pad..) that I must make the two world’s intersect at some point by introducing you to each other. You’re both super smart and funny and delightfully lovely so I utterly fail to see how you wouldn’t love each other IRL.

    Anyhoo, back to the matter at hand… I agree with Di re the kissing. I think zero kissing on date two, now that a precedent has been set, would make him think you don’t fancy him after all. So, if you do, at all, then that could prove problematic.

    I do, however, agree with David re the exclusive conversation. Oh for the days you just hooked up, got together, and that was that…. But more and more people these days do seem to be juggling multiple dates (thank you RSVP), so you can’t assume anything until you’ve actually laid your cards on the table.

    As for the pilot, he may well be all the more attractive because he isn’t (as yet) so available. As these things go. I think you should definitely give ol’ twinkly a bit more time, because he sounds lovely and his reference check was lovely, and you just never know what, if anything, will happen with pilot guy.

    And, as I said, if you date them both simultaneously you won’t be as fussed about either, which will make you all the more desirable to both, because that’s also how these things go.

    I eagerly await further updates….

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