When Dating Philosophies Collide

July 15, 2010     Posted in Advice, Relationships

Recently, I met a guy. (Whew, crazy right?!).  I met him at work – he was visiting the racetrack (I work up in the press box) with a large group of his buddies.  They were enduring a bachelor party so had shimmied over on a nice little margarita buzz. He approached me and asked for my number.  He kind of resembled Sean William Scott and was super sweet, like the smell of tequila coming out of his pores on his breath.

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Smitten, I scribbled it down, hoping I put the right area code. I didn’t expect him to call me that night because I was convinced he was at his tenth strip joint, but when he called me asking what I was doing my hopes took a high ride. We talked for a little bit, but his bachelor party activities got in the way of us hanging out that night (probably because he couldn’t figure out how to get a thong untied from his face).

And now, this girl needs some serious Dating 101. Unfortunately homeboy didn’t ask me to hang out/go on a date beyond our brief bachelor party convo and now all I want to do is ask him myself.

But here comes the battle of my two dating philosophies:

My Dating Philosophy #1: ‘Tradition is Key”
I’ve always been more traditional and it’s annoying. It has worked and hasn’t worked in my favor. I always want the man to make the first move, because then I can be sure he digs me.  I’ve always felt more safe that way. Why would I waste time asking questions like; “Nope, he doesn’t like me because he put his hand in his pocket and looked at the ground when he said goodbye…”

If the guy asks me out, you know he wants to see me, right?  But if I ask him out – I really don’t know for sure if he’s giving me a pity-date just because he doesn’t have the heart to say no.  I guess my pride has roped in the best of me.  We all have an itty bitty tendency to stick up our nose and bask in the satisfaction/fantasy land that I’ll be fine, the man I end up really loving will ask me out himself.

From what I’ve learned, guys are pretty simple.  If they like you, they will ask you out. If they don’t um…they won’t.  In the end, wouldn’t you want a confident guy that is going to jump forward and make the first move anyway?

My Dating Philosophy #2L “It’s 2010-You-Are-A-Big-Girl?”
What do I have to lose? You get what you want in life because you go out there and get it yourself. I’ve been riding easy on the quote, “You have to go on a limb sometimes  because that is where the fruit is.”  It really is true; you have to put yourself out there or how are you going to ever know if ‘it was meant to be.’  Besides, what is the worse he could say – ‘Um no?’ His loss anyway.  Guys nowadays like a confident girl who can bust out of the realm and ask someone out.  It is that simple.

Recently, my the other lovely intern in the press box gave me fabulous advice – and yet another great philosophy. She said, “I say you ask him. If he say’s yes and he likes you, than great! If he say’s yes and doesn’t like you? That is his problem that he has to sit through an entire movie with you.”

So true. But I’m still stuck in a rut. And the rut usually consists of staring at my iPhone screen and constantly deleting attempted text messages. Do I ask him on a date myself – shamelessly – and risk the ability to know if he really digs me? Or do I sit duck and wait for his phone call, knowing for sure that he’s into me if he does?

I need some help here! Which philosophy do I loyally follow??

20 Comments on "When Dating Philosophies Collide"
  1. CR says:
    Thu, 15th Jul 20101:54 pm 

    I am constantly stuck between these two philosophies! One half of me is in entire agreeance with you, I like to wait for the guy to put himself out there so there's no doubt in my mind. But the other half has been known to send some really outrageous text messages and hop in the nearest cab to go after what I want (usually after some liquid courage – but this has never ended badly!) It's just hard to know where to find that middle balance of putting in effort but not looking desperate!

  2. grace b says:
    Thu, 15th Jul 20102:00 pm 

    I'd say #2 all the way. I know too many girls who rely on #1 and end up really dissatisfied in their relationships as well as lacking the confidence to be single or to approach a guy first. Guess that's just the way I prefer it.

  3. Bailey says:
    Thu, 15th Jul 20102:56 pm 

    Seriously! I think every girl is plagued by this. In college and beyond, it's all "should I be a feminist and ask him?" and you just never know what to do. I finally sucked it up a few months ago and asked a guy on a date, and he said yes, but apparently it was a no go because he canceled the day before. Boo! Right? So…that was kind of a bummer…but now I'm feeling a bit more adventurous, like I'm in control. It's good to know, anyway.

    But on the whole, I think you can pretty much tell when there's something going on, and if there is, go for it. You know in the pit of your stomach what the real situation is, and you should act on it (or not, if you know he doesn't like you, but we'll go with he does). If you know you've got it goin' on, ask him out. It doesn't even have to be a Date – just ask him to hang out. He'll get the picture!

  4. melissa says:
    Thu, 15th Jul 20103:01 pm 

    Oh god. I was in this position tuesday night.

    Cute guy at work asked for my number on last monday. we made plans for wednesday and hung out. Things went really well//we both had a great time.

    The rest of the week he continued being flirty/wanted to hang out again friday night. But I promised my friend I would go out with her, so we couldn't hang.

    Tuesday night I racked up the nerve aka grew a pair of balls and texted him asking if he wanted to hang out this friday (tomorrow) and he hasn't texted me back. WTF?

  5. AGuy says:
    Thu, 15th Jul 20103:02 pm 

    He was drunk and probably thinking "I have a pass from the GF for the whole night! I'm going to bake up some post-bachelor-party pork pie!"

    So he DID ask you out by calling you. You and the other 49 chicks he hit on that day had an 8-12 hour shelf life, that night only.

    When you waffled (and you know you did) he kept dialing until he found one that was more responsive. Or he passed out in a pile of puke.

    The moral is: either tradition or you-ask-him will work, but the clock is ticking!

  6. Timothy says:
    Thu, 15th Jul 20104:11 pm 

    If a girl asked me on a date, I'd absolutely say yes. I'm definitely willing to spend a few hours with any girl who has the guts to ask me out; I don't mean to sound arrogant, it is just obviously an intimidating thing to do, particularly if it isn't something she's used to doing.

  7. Ke says:
    Thu, 15th Jul 20106:25 pm 

    I say the second philosophy, just because that way you are wasting less of your time. If he chooses to waste his, by saying yes when he doesn't want to, then (as noted earlier) it's his problem. Plus, from what I've noticed, some guys like the girl making the first move, since stereotypically there's a lot of pressure on guys concerning dating anyway and just like you feel confident when asked out, some guys need that too :p

  8. manonymous says:
    Thu, 15th Jul 20108:28 pm 

    i don't think there's anything "feminist" about asking someone out, but if that's the way you need to think in order ask out someone, then ASK HIM OUT YOU DUMMY!

  9. Krystle says:
    Fri, 16th Jul 201010:12 am 

    sounds like a trophy number to me..

    then again he did follow up and called you..but NEVER SET A DATE.

    it sounds like he's not fully interested..but how can he..if you guys haven't had a full on conversation yet.

    SO…BE THE BIG GIRL AND ASK HIM OUT..if you think he's worth it. I guess it comes down to the question of-Is the lemon worth the squeeze? ;) haha GOOD LUCK GIRL

  10. single and ready to says:
    Mon, 19th Jul 20103:58 am 

    it's difficult isn't it?

    I am just easing back into the dating world (and blogging about it!) and I can't figure out how to strike a balance. Sometimes I think you have to let them come to you, but other times, I think you can go after what you want. Life is all about doing what you feel you need to do–and if it's meant to be, it'll work out perfectly. The only down side to putting ourselves out there is that it might result in pain. But if you don't put yourself out there…how will you ever know?

    http://theblindleadingtheblonde.wordpress.com

  11. misnomer says:
    Mon, 19th Jul 20108:15 am 

    I like your coworker's philosophy. Although I also get wanting a guy who is confident enough to know what he wants. But, that may be a dream so I say ask him out.

    http://studentswhostillhavesouls.blogspot.com

  12. OldFashioned says:
    Mon, 19th Jul 201012:50 pm 

    I just had to comment on this one given that I am "old-fashioned". If you want this to go anywhere don't bother asking him out-it won't work. If he was interested in dating you he would have asked you out when he called you. If you do still think you might like him you could just try and keep in touch and see if he asks you out from there. Send him a cute text or something asking how the bachelor party ended up or something

    But in general asking a guy out doesn't really work. He knows he doesn't have to try. I'm not saying this happens 100% of the time because I'm sure there are exceptions.

    Besides you'll have to pay if you ask him out and that's just strange to have a girl pay on the first date

  13. Hannah says:
    Wed, 21st Jul 20106:45 pm 

    Asking first can honestly work, and no it doesn't mean that the guy is not ballsy or interested enough in you. My current boyfriend and I had been hardcore flirting for a month and both of us finally got to a point where we were dying to go on a date with each other. He had attempted to ask me out, but unfortunately had called me at an inopportune moment for what was going to be a spontaneous casual date, we both got jumbled from nerves and I had said something along the lines of 'another time'. I am absolutely notorious for sounding aloof on the phone, so I texted him the next day with an invite to meet me at a Thai place, and when I got the conformation that he could make it, I was on cloud nine.

    Moral of the story, it doesn't matter who asks who if you like each other.

  14. MelodicBrush says:
    Thu, 22nd Jul 20101:03 am 

    This coming from a handsome young man with a nice salary and with the qualifications required to be a 1st class knight, go with #1, if they dont dig you enough to ask you then say yes to you asking them then they either arent ready for a relationship or just pity you enough to have sex with you then leave.

  15. misnomer says:
    Fri, 23rd Jul 20109:10 pm 

    The thing is, what if the guy is thinking, "If she liked me, she would be giving me more of a clue." The guy could just be shy or nervous, so I'm sticking with my original answer: go with it.

    http://studentswhostillhavesouls.blogspot.com

  16. Kelly says:
    Sun, 25th Jul 201011:08 am 

    love the philosophy of your fellow intern. its nice for him to put himself out there, but we need to take a page from their book sometimes. in fact it just inspired me to ask someone I've been interested in out on a date. :)

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