A few months ago I was in Rachael’s king size bed fretting over sending a very forward propositional text message to someone I thought was foxy. “C’mon Bev, nobody ever died of awkward. Worst case scenario she’s flattered and says no.”


I sent the message and the response I got was articulate, complimentary and offered a raincheck. Kelli Dunham, Butch Comic in Residence for FemmeCast asked if this person had taken classes on how to write text messages because it was so good.

But more than the response, I was really proud of myself for putting myself out there. Zoe beats it like a drum everytime I do something like this.

Half the reasons I’ve missed out on getting ass in my lifetime is by not articulating my desire. Insecurity, fear of rejection, fear of being made fun of… the list is endless. It’s hard to put yourself out there in a racist, homophobic, misogynist, binary gendered, anti-erotic, fatphobic, ableist, etc… society when you’re at one or many of those intersections of marginalized identities. Plainly stated, I’ve been a fat girl my whole life, shit from middle school runs deep and it’s hard to bounce back from significant early rejection.

Out of that insecurity can come a bevy of reasons to psych yourself out of propositioning someone.

After that moment I incorporated “Nobody ever died of awkward” into my regular on stage repetoire. As any of you who have seen me femmecee can attest, I am a fan of encouraging my audience to interact after the show or during intermissions. I often give out pick-up lines, conversation starters and ways for people to connect. I love matchmaking.

At the Zombie Queer Cabaret this weekend someone said I was easy and I said, “I’m not easy, I’m just straightforward.” When I’m attracted to someone it can often inspire in me my old shyness. In fact, one of the signs that I’m really into someone I’ve just met is if I have a hard time looking them in the eye (though I am working on getting over that). The shyness is really just insecurity. The fastest way to get through that shyness, for me, is to just be direct.

I still have to go through the same cycle of insecurity I always have when I proposition someone, but now I can psych myself up about it way faster than I ever could before. I’m talking a matter of hours versus days, weeks or months. In college it would take me weeks to work up the courage to ask someone to hang out as a friend-that-might-lead-to-more. Now I might let a passing interest develop into a crush for as long as a month, but there’s a certain moment of annoyance I reach when I am getting mixed signals from someone and I just want to cut to the chase.

When I ask someone out I always use the term “date”. I encourage you to do that, too. My friend Megan Beene used to complain about the “Lesbian Not-Date” syndrome where you’re hanging out with someone and you’re not sure if it was/is a date.


I like to make sure it’s clear what my intentions are. I also often tell them that my intention is “casual” or “proper” date.*

Even if you’re not asking someone out and just expressing interest, it is really great to be direct. One of the greatest examples I’ve experienced was really more of a gesture than the words themselves, but this really hot butch I’d been trying to make contact with for 2 weeks came up to me in the dark, put her hand on the small of my back as she walked by and said something in my ear along the lines of me being a really attractive woman. And then she walked away. I don’t even remember what she said but it was really clear.

The best part about having a move like that is that no matter how nervous you are, you’ll never actually seem that nervous in person. Trust.

Another thing I always do when I ask people out is to be complimentary and to not give them the reason to reject your offer. If they want to turn you down, they can, but let them be the ones to come up with the excuse.

An example is “Georgine, I’ve found our long talks about homo fashion really intriguing and would love to continue the conversation. Would you like to go out on a date with me? I am thinking a casual walk along the Christopher Street pier where we can see the fashions of the gay youth of today followed by a coffee at the one remaining West Village gay coffee house.” Instead of all of that followed by “Unless you’re busy. It’s really okay, you know, if you’re busy. Or if you don’t want to. Or if you want to just be friends.” If they want to be friends they can propose that with their proper response to you.

I tend to also be really cutesy with my date requests and use a little schtick. A friend of mine uses rhyming, which is particularly adorable. I like to think putting some personality in the date request makes it all the more flattering, and that is what a date request should ultimately be.

Rachael’s flirting philosophy is “It is never a bad time to make people feel good about themselves.” I think this absolutely applies to asking people out.** I have also found that the fastest way for me to get over a crush is to be rejected by them. And, really, how can you be into someone who doesn’t think you’re fabulous enough to date?

It’s comical how many of my friends I once asked out or who once asked me out. In every one of those cases it was clear within a few months that it was way better that we chose the friend route.

The awkwardness lasts as long as you let it, and I purposefully act like nothing is wrong until nothing really is wrong anymore. It’s best to just try to be normal.

What I love about having gotten a lot of practice asking people out in the last couple of years is that now it comes much more naturally. I met this hot girl last month and after flirting with her a few times in the evening as I was bidding her adieu and we exchanged numbers I told her straight up “If you’re interested in asking me on a date I would love that.” (Sometimes the butches like to do the asking.)

The important part is that you see your success as battling your insecurity and putting yourself out there, rather than what the reaction of the other person happens to be. You’ll always be successful when you push yourself to grow.

Today on Twitter, Shit My Dad Says tweeted “That woman was sexy…Out of your league? Son. Let women figure out why they won’t screw you, don’t do it for them.”

So the next time you are getting an attack of insecurity about a crush, or you aren’t sure whether you should ask someone out, stop thinking and start texting/emailing/calling/talking and do it. Let them make the decision whether they will go out with you. You won’t die of awkward if they say no.

*I’m going into much greater detail about this in the episode of FemmeCast I’m editing right now, on courtship.

For me a casual date would involve a meandering hang out, a variety of outside activities, watching a movie at home, having cupcakes together. Something easy and cheap. I often prefer casual dates because I lead such a fast-paced life, what I’m looking for in a potential dating person/girlfriend is really someone who its easy and fun to be around. Casual dates help to tell you that.

A proper date is something more traditional. A performance and drinks, dinner and a movie, just dinner. Some of the best dates I’ve been on involved an activity that told me more about what the person was passionate about and had a sweet and small souvenir.

**Of course, this is NOT the case for those who are monogamous or you are otherwise ethically barred from dating, like your friend’s recent ex or some such close queer connection. Let ethics not insecurity slow you down!

16 Responses

  1. I LOVE this post. I have been partnered for 15 years so don’t have the fun of dating anymore, but I think this can apply to other situations. Especially the “no one ever died of awkward” mantra. This is fabulous stuff! I smiled the whole time I was reading it, remembering how fun dating was. I think I’m going to start dating my partner again. We could use an injection of flirt/date energy.

  2. It’s harder if you aren’t sure when your lady interest is into women… Living in rural Kansas queer dates are pretty murky waters. Boo 🙁

  3. So….you think texting is an ok way to ask a friend out or tell her you’re kinda into her? I’m a baby les and I’m terrrrrified of rejection or making a move. I’ve never done it before. I’m getting positive and negative signs from the girl I like. (she is gay and single). I just don’t want to look like a chicken s*it, but my friends are saying if she likes me it won’t matter so….. I don’t know

  4. This was a delightful read!
    My wife, also a hot curvy femme, was direct with me and now, well, we’re married!
    Her “end of first date line” was ‘are you really fumbling for your keys or do you just wanna kiss me?’ who could say no to that?!

  5. I can say this is true. I’ve asked out a friend, still interested even if their not, but I’m not finding it that awkward… Except when they were suppose to visit, then it “didn’t work out”, through it probably was that, but felt awkward because they were supposidly going to stay at my house or something.

  6. I just stumbled upon your blog randomly. I’m devouring your entries voraciously, but I had to comment on this one in particular because, seriously?

    Best. Dating advice. EVER!

  7. Did the FemmeCast episode you mention here (on courting) get released? I don’t see it, but I’m kinda new to your blog/site/etc.

    1. Oh M. I took an unintentional hiatus from FemmeCast for the last few months, but I’m back and working on it now! It’s been recorded and ready save for editing for a long time! I’ll announce it as a blog entry here @ QueerFatFemme.com and on Femme-Cast.com!

  8. I am personally a very shy and awkward person but I’ve been trying to take more control of my life and get over it. This article is inspiring because it shows me how I’m not alone in these feelings and it might just give me some confidence to try doing the asking for once knowing that half the room probably feels the same way I do.

    Thanks for the advice!

    1. This is super true, especially if you consider that I myself am anything but quiet in typical circumstances, yet I still have to rally my personal troops every time I want to get up the gumption to ask someone out!

  9. Yes, a million times, yes, to all of this.

    Its really hard to get up the gumption to ask someone out on a date, and sometimes it doesn’t even work the first time, but I’ve taken this advice from you before, and its good advice! I can’t wait for the femmecast episode on courtship!



  10. My philosophy, which I fully credit to the teachings of Deb M. and Holly H. from their NOLOSE 2004 workshop “The D Word,” is that it’s all about playing the odds and about doing for self.

    To elaborate: For many of us, we refrain from asking someone out/going for something or someone we want because we’re afraid of rejection. And rejection does suck, no question. But, for every risk we take, even if the result is rejection, over the long run, we will end up with many more positive results than if had we done nothing.

    Think about it like flipping a coin: if you’re afraid to end up on “tails” and so you don’t play, you won’t *ever* end up on heads. But if you keep flipping that coin, sure you’ll get some tails. But you’ll get a lot of heads too, especially in the long run.

    Moreover, the more risks you take, the more you’ll learn to let rejection roll off your back because you’ll realize that it’s not the end of the world and life goes on. This will take a lot of the pressure off of going after someone/thing you want.

    Further, focus on the “doing” not the results. Make the goal the taking of risks and then it’s win for you no matter what. With that as your goal, the more risks you take, the more you’ll come to think of yourself as a confident person who fearlessly goes after what she or he wants.

    An additional benefit of this strategy is that you won’t waste hours, days, weeks, months agonizing and ruminating about “Should I or shouldn’t I? This person did X which could be a good sign but then they also did Y so I don’t know…” Aaaaaahhhh! Get yourself out of that angsty headspace! It might be good for brooding poetry but otherwise it’s pretty useless.

    So go after what you want and take a lighthearted attitude toward it all. Life is too short to do otherwise.

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