22 June 2008

Who has two thumbs and sucks at flirting? This girl!

By: Jessica B.

You may think I’m kidding, but I’m not. I suck at flirting. Let’s take Saturday night as another shining example of this point.

Scene: Unnamed Lakeview bar and grill, me entering to pick up a carry-out order. Dressed in an Old Navy tank top (with a small smoothie stain I discovered later), bra strap exposed, looking very warm and flustered from the heat and wearing a cotton skirt with little make up on. I go up to the bar to pick up my order and two nice-looking guys are sitting at the bar as well. Non-spoken descriptions are below in italics.
Guy 1 (the blonde-haired guy): Looks at me, gives me a warm smile, which I return. Hi there.
Me: Hi
Guy 2 (the dark-haired guy): Also looks at me and smiles while Guy 1 continues to throw looks my way. Hey there.
Me: Hi
Bartender: Okay here’s your order. He tells me the amount and I hand over my credit card, Guy 1 and 2 are still smiling at me, which I continue to smile back.
Me: Thanks, turns to Guy 1 and 2, have a good night giving them my patented “look”
Guy 1: You too, I leave but can feel someone watching me as I go. Tempted to turn around and give one final look and smile but do not.
End scene
Okay so that might not have exactly been me flirting and of course there is the likely possibility the guys were just being polite and watched me walk away out of horror for my outfit choice. Either way, the entire way home I’m kicking myself in the a** for not saying more to them or really anything. These guys were cute! But as I walk home, cursing, I realize I can’t go back because they’ve seen me with a carry-out order so if I go back I’ll be a) psycho for going back to ask about some asinine thing with my food or b) obvious that I would like them to ask me to stay for a drink or offer to join them. What is my problem?
And yet again I have solidified the fact that I suck at flirting, mostly because I still have a hard time believing a guy would want to flirt with me. I really not trying to be self-deprecating here but I’m totally serious! I am awful when it comes to guys because I have no idea what to say to them or my snippy, sarcastic humor ends up scaring them away or putting me in the “friend” category almost immediately. I’m the buddy, the wing(wo)man. Guys talk to me to get to one of my friends. It’s so true.
Here’s another solid example of my poor flirting skills. Right after college, I was living in Wisconsin and could not find a decent job to save my life. So one night, I go out with my friend for her birthday and I end up hammered and making out with her boyfriend’s friend at her apartment. While this guy and I are fooling around, he whispers to me, “what do you want?” And I sh*t you not, this is my drunken answer, “a job.” Really, I’ll let that sink in for a moment because that is what I said without even thinking. And his response? “I can’t give that to you.” And thus the fooling around was done not long after that comment.
This guy would have done anything I asked him to with his mouth or hands or both, resulting in my toes curling and likely being rendered speechless and my answer to him is, “a job.” In actuality, I wanted him to do something with his hands or mouth to take my mind off not having a job, but apparently I could not communicate in the heat of the moment. My friend could not stop laughing when I told her that. It was embarrassing. 
Once after a night out in Chicago, I had a guy offer to take the bus home with me, even though the El would drop him off closer to his house, and my comment to him was, “why would you do that?” My friend Sarah, who was trying to set me up with this guy (who is now engaged to someone else), looked at me like, “Jess do you seriously not see why he would do that?” And my answer was yes.
So next weekend when we’re out, my goal is to turn off the inner monologue long enough to give flirting a real try without sounding like a moron. And I’m actively recruiting for my own wing(wo)man so let me know if you’re interested in applying. References are appreciated.

33 Comments

  1. Kali says:

    Found you off Survivor’s blog..

    And laughed out loud at the ‘job’ comment.

    Thank you for making me look like a moron (I am a receptionist at the front desk)!

  2. Fabulously Broke says:

    Uh I’m that way too. I am actually more naive than dumb at flirting. I don’t actually KNOW they’re flirting with me.

    Maybe try “How’s it going” next time? :)

  3. Melissa says:

    Everyone’s talking about the “job” comment but sadly, I could see myself saying not just that [brilliant!] one but the others you listed too.

    I never really thought about how I was at flirting. I guess it doesn’t bode well that I could see myself saying ALL the same things you did!

    PS: Got here through your comment on Vanessa’s blog. I was curious about the “cupcake crawl” :)

  4. mindy says:

    Oh dear, your flirting methodology sounds suspiciously similar to mine. I am very sorry for you about that.

  5. Ashley says:

    HA. That was THE funniest thing I’ve read in a long, loooong time.

    I definitely laughed aloud. I want a job. :)

  6. Blaez says:

    i suck at flirting too… thankfully i met joe online throug ha game we both like to play. it’s easy to flirt in a game :)

  7. redstaplernation says:

    I am completely jealous of this Chicago meetup and I will be bitching mightily into my beer on Friday night.

    But I will be wingwoman for you on Friday, August 1st! I think there’s free wine at my hotel that night too, and flirting is always more fun when your speech is slurry :o)

  8. Anonymous says:

    The wascally wabbit is your friend. If you don’t have one — go get one. Bzzzzzzzzzzzzzz ;-)

  9. Princess Pointful says:

    Okay, you seriously had me laughing out loud with the job comment. Too funny, my dear.

    And I was totally at the Bean today and thought of your blog! It is pretty much the coolest thing ever (the Bean… and your blog ;) ).

    See you soon! Eek!

  10. Angela says:

    I’m ALWAYS the wingwoman, and I HATE it sometimes! I just want to be the one that guys want to talk to for a change, yannow??

    Anywho, asking for “a job” is a pretty funny story! But hey–you were wasted and not thinking straight. So don’t be too hard on yourself! You’re just shy–like me! But DAMN do I want a guy to flirt/makeout with.

  11. Erin says:

    Hahaha! A job? That’s brilliant. I probably would have said the same thing!

  12. megkathleen says:

    Hey, those guys weren’t the greatest flirters either! I used to always have go-to lines I would use when I saw a cute guy. But I’m the worst flirter so I never delivered them well.

  13. Marianne says:

    NO! Can’t believe the horror of the job comment. But I’m hearing you, it’s really hard to flirt, I feel too cringey doing anything like that. And I’m ALWAYS the one guys befriend to get my beautiful friend. Good luck this weekend!

  14. lifeintheleftlane says:

    Oh no! That was awful, and I laughed…sorry! :)

    I suck at flirting too. When I was single, I would clam up around hot guys and act strange. When I didn’t feel an attraction to a guy, I’d be super flirty and never even realized it.

    And supposedly I’m a bad wing woman because I talk to everyone and am too nice since I’m not looking for a guy anymore (that’s what my single friends tell me).

  15. Jenn says:

    I’m definitely voting Maxie as the wingwoman!

  16. Chelsea Talks Smack says:

    DUDE, I suck at it too. I totally feel you.

  17. L Sass says:

    Oh man, I TOTALLY would have said that I wanted a job, too. Ouch!

    It is so hard not to be self-conscious while flirting! But I hope you got some in this weekend and it went well!

  18. surviving myself says:

    Listen – no loss for you. Any guys that would lead with “Hi there” are probably not worth talking to.

    If one of them had said something like, “You know, I can make a really mean PB&J sandwich.”

    That’s someone worth flirting with.

  19. kay* says:

    LMAO “a job” that is classis! oh my gosh. but seriously – i hear you on that: always kicking yourself AFTER the moment has passed. i do that ALL the time! make eye contact…smile…then walk off thinking ‘WTF did i just do that for!’
    seriously – if you find a good wingwoman send her my way too :o)

  20. wontletlifedefineme says:

    I’m okay at flirting, but not at talking to guys – so usually for me to be successful at flirting+ some form of dancing has to be involved.

  21. nuttycow says:

    I know it’s been said to death but I *also* love the “job” comment. I can just imagine his confusion.

    Don’t worry about the guys. They’ll be back. :)

  22. sandy says:

    Haha, that job comment is way too hilarious.
    My problem hasn’t been that I suck at flirting, it’s that people always seem to think that I AM flirting.. when in reality, I feel like I’m just being friendly. This tends to get me into trouble.
    And no, I won’t be hanging out this weekend unfortunately- it’s my brother’s college grad party at my house & I’ve got tons of relatives staying with me. Blah. The ONE weekend! But sometime soon there should be another outing planned, yes?

  23. Joy @ Big Time Fancy says:

    Wiiiiiiiiiiiingwomannnnn!

    I promise that I will personally lift you up and throw you at boys next Friday.

  24. EP says:

    Umm, I’m right there with you. I’m incredibly awkward when it comes to flirting for the same reason — I’ve always been the wing(wo)man. :/

    Apparently, the first time I stayed at my boy’s home, he asked me if it was going to be awkward. I turned to him and said, “I don’t know. But I kind of like awkward.” Of course, I don’t remember this, but he told me about it this weekend, stating that was when he knew he liked me.

    So maybe being awkward isn’t all that bad?

  25. ANG* says:

    oh man – i can TOTALLY relate to everything about this post. flirting + me = disaster. i’ve actually stopped trying its so bad.

    and AWESOME “job” comment. love it :)

  26. jenniferalaine says:

    Check Craigslits “Missed Connections” for the guys at the bar! I’m obsessed with it. A little unhealthy, perhaps, but amazing nonetheless.

    And echoing everyone else’s comments… The “job” answer is hilarious. Love it.

  27. Rachel says:

    that job line? AWESOME! I can just picture all the different sexual acts going through his mind like a roladex.

    “Job, job, job, job….what the hell is she talking about?’

  28. Alexa says:

    so yeah i kinda have the same problem. i guy will blatantly be flirting with me showing all sorts of interest and ill be like, “so i have this friend that you would be GREAT with”

    um yeah, that’s not going to help my singledom.

  29. brandy says:

    The job comment made me laugh out loud! That would definitely be so something I would say too. I remember this hot guy Clint had a locker right beside me in grade 10. He was new to the school, which just made him even more mysterious. He was always teasing me, so finally I asked him ‘why are you so mean to me all the time?’. I was dead serious. He looked at me and said ‘Brandy, I’m flirting with you because I like you”. And because I am who I am, I followed up that up with an extremely puzzled ‘why?’.

    I cringe just thinking about it.

  30. thegoodnamesaretaken says:

    I had a guy try to open a car door for me but I got so confused by him walking to the same side of the car as me that I started walking around the next car. He finally had to tell me (in an exasperated voice), “I’m trying to open the car door for you!” Haha. I’m not too smooth with the guys either :)

  31. Tipp says:

    I vote Maxie for wingwoman.

  32. Maxie says:

    um you will have many, many bloggers to pick from friday night. And i’m a fantastic wingwoman.

    The job comment? hilarious. Hey- at least you were telling the truth.

  33. thatShortChick says:

    i’m in tears due to that job comment. i hate to have a laugh at your (drunken) expense but, dear lord, that was funny.

    i hear you on the whole not good at flirting thing. i become a mute in the prescence of really cute guys and cannot produce an intelligent sentence if i tried. it’s insanely ridiculous.

 

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