Thursday, February 21, 2013


Last weekend, I think I got a small taste of what it's (maybe? sort of?) like to be a guy. At least, a single guy at a cool Brooklyn bar on a holiday Sunday evening. 

I want to tell you a story. After I do, let's talk about this whole "putting yourself out there" thing.

Rachel and I were out fetting her boyfriend's roommate who was moving to Berlin, and nobody had to work the next day. There were whiskey cocktails and introductions all around. One of the group, a girl sitting up at the bar, ordered an Orange Manhattan, which was served up, in a martini glass. She let me try it and it was delicious, but I have a strong aversion to martini glasses. (Precarious and pretentious unless you're having an actual dirty martini.) The bartender asked if I wanted it on the rocks in a tumblr and I was game.

Not much later, over the rim of my newly rocked cocktail and through the crowd, my eyes landed on a real gem: blackwatch flannel, slim khakis, perfect teeth. He was talking to a group of guys who were also not bad looking. Something came over me and - bolstered by my manhattan and a brief pep talk - I decided to approach them.

"I need you guys to help me settle a bet."

[Inquisitive looks, chuckles, attention.] "Okay."

"Is it poor form to order a Manhattan on the rocks?"

Apparently not.

The rest of the small talk isn't really important - the point is that I got them (and especially the gem) talking. Graphic designer. Great hair. Lives in Brooklyn? Something something those teeth. Anyway we're chatting, we're vibing, and his friends are telling me I have to come out dancing with them. 

From a distance Rachel texts, You're killing it over there!

In my head I'm like, "Yes. I am killing it. I am hitting on these guys and it is working. I'm reversing stereotypes and putting myself out there. Ball in my court and everything. Look at me go in twenty thirteen."

Next thing I know these guys are making a play for the next bar and the gem with the teeth goes to retrieve his coat. He comes back wearing a varsity jacket almost identical to mine and carrying a skateboard. I may have visibly rocked on my heels.

[Weird side hug.] "Well, nice to meet you..."

[Bat lashes.] "Yeah... You too."


Yeahhhhh they just left. No numbers exchanged, nada. All that effort and coy banter and becoming convinced I had met my next first date -- I'm back at the bar with Rachel ordering a second manhattan.

What the hell, man? I was wooing you!

No, I didn't ask him if it hurt when he fell from heaven and offer to buy him a drink -- but I threw out a line. I rolled solo and threw out a pick-up line. Guys (really, actual guys), that is not easy.

This wasn't the first time I've made the first move in approaching a guy. But, the bittersweet experience definitely reminded me that putting yourself out there in an effort to meet someone new can be both terrifying and a little fun. Sure, I didn't get any numbers or even so much as a wink goodbye, but I also didn't die. So, there you go.

Gals, do you find it hard to put yourself out there when you're single? Do you approach guys when you're out? Guys, is this kind of experience as disappointing for you as it was for me? Bravery, flirting, rejection... Let's talk.


  1. you are so funny & such a good writer---- keep at it and i think that the RIGHT/COOL guy will ask for your number, or at least really invite you to the next bar with him.


  2. First of all, I love this. Second of all, bravo! I'm highly impressed. The perfect opener, well-played banter and you didn't make a fool of yourself. Number or not, I consider that one successful play.

  3. HAHA! I love this!!!! i find it extremely difficult to talk to (hot) guys at a bar.....unless ive had a couple drinks! I am newly single so i havent done this in a while....*sad face*...BUT ANYWAY you just reminded me of exactly how fun it can be....cant wait to get out there again!

  4. i just loved that story, it is one the reasons why i am so fond of your blog. keep posting things like these, i mean, i love this type of posts. i think it's really hard to put yourself out there since when you are single and want to know someone, the guy already has a clear idea: either he is really trying hard to meet someone to settle or just wants a one night stand and it seems like there is no in between for them.

    keep it up xx

  5. I love this post so much! I don't think I've ever actively put myself out there such as you in this situation. I've done the real mature talk to the friend thing, "Hey what's your buddy's name?" while he's at the bathroom. I think it's a good 2013 goal to pursue a little more rather than hoping something will happen. Like you said, you/I probably won't die from it.

    And whiskey is my favorite so I'm sure I'll have no problem with that. Thanks for the motivation.

  6. Yes, yes, a thousand times yes! This has happened to me on several occasions, even when the guy was the one who approached me first. On one particularly gruesome turn, after an hour of great conversation and multiple affirmations from him about how beautiful/smart/funny he though I was, we exchanged numbers and parted with plans to hang out the next day. And then? Nada. Not a word from him. Part of me wonders if it's like that episode of SATC where Miranda gets mad at a guy for not calling her and it turns out he died. A bit morbid? Maybe. But hey, that's life. The important thing to remember is that you're a BAMF for taking things into your own hands and that he was to big of a *other word for cat* to man up and ask you out.

  7. This cracked me up - From the title I wasn't sure what to expect but I think this is a great line. I play wing-girl a lot for both my male & female friends so I know how rough it is when no numbers are exchanged - You should have asked! You started the conversation, maybe they were expecting you to take the next step...

    P.S. EVERYONE needs a graphic designer in their life!!!

  8. Yes! I have had a crush on a guy at work for a while so instead of waiting around for him to ask me out - I asked him! It was so out of my comfort zone but a little liquid courage and some sass will get ya a long way :)

    Bad news was that I actually had to plan the date, which was really stressful! I never gave guys enough credit for planning a first date. But I figure it'll be a cute story to tell our kids one day haha (mostly kidding...)


  9. Ha, I loved this post. It sounds like that is pretty much what it is like to be a guy! Dating is hard, but finding a date is even harder. Good luck! And no, it is not wrong to order a Manhattan on the rocks.

  10. This is one of the greatest things I have ever read. You are hilarious. Way to be ballsy! Sometimes I think guys assume you will just run into each other again by chance. But life is not like a sitcom, so lets remember to exchange cell phone numbers people. - Megan

  11. I love the dating posts, they're so brilliant!

    On the subject of putting yourself out there, I actually tried this on Valentine's Day...I was at a bar eyeing up a gorgeous blond Macklemore doppelganger, who came over to me, put his arm around my shoulders and asked my name. I batted my eyelashes, affected a coy smile and said, "That information will cost you a drink." He replied, "If you had told me your name, maybe I would have bought you a drink after"...and walked away, never to return. Consider my self-esteem somewhat crushed.

    Moral of the story, putting yourself out there is hard and I'm proud of you for taking the leap, Taylor! The world needs more girls like you

  12. Omg I love this! aha I do salute you for taking the leap because I find it soo hard ok maybe being a 15yr old girl you could say it doesn't count but sometimes in situations like those I literally play out like entire conversations in my head how I would say cool funny lines and how they would respond and we'd have like amazing conversation ahaha but they never actually happen cus I could never just walk up to guys and say whats up or could I aha I think you may have converted me! In your situation hun so what if he didnt ask for your number he obviously isnt the right guy if he can't even notice a ballsy amazing girl when she walks right up to him aha Lovely post dear xox

  13. Can I just say this is a perfect example of why I've been faithfully following your blog for nearly three years?? You're hilarious, and I love reading your personal stories mixed with fashion commentary. Pure. Delight.

  14. I love that outfit!!
    Much love,

  15. You should post on Missed Connections and see if you get a hit...

  16. I'm the worst when it comes to approaching a guy (ie. I don't) so kudos to you girl. :) Maybe they assumed that since you seemed like a confident, outgoing, cool chick, that you would just make the next move yourself...or maybe they were slightly intimidated..? Who knows? But I think most men admire/love a woman who would do what you did! So nice work.

  17. I LOVE THIS! Kudos to you for putting yourself out there! You've inspired me..maybe I will get over myself and do the same!