Popping the Question: D’s Hindsight is Awesome Tips for Asking Out Your First (Gay) Date

The outpouring of support for the It Gets Better Project and all the other efforts to address teenage suicide as a result of bullying has been absolutely freaking awesome. Like, really. Keep it up, keep spreading the word, keep making it better.

I am not going to be nearly so depressing this week! I promise.

Readers will know that I am obviously the gay dating queen because I ended up gay married. Obviously. This is also totally false. I was generally pretty bad at dating. Well, mostly the first dates. And the run up to the first dates. And the flirting. So, I present D’s Hindsight Is Awesome Tips For Asking Out Your First (Gay) Date.

D’s Hindsight Is Awesome Tips For Asking Out Your First (Gay) Date

Figure out if they’re into you like you’re into them.

Now, I am no expert, but I am pretty sure that most straight people do not spend a lot of their mate selection process wondering if their potential date is, in fact, interested in their entire gender. But that’s what happens when your dating pool is less than ten percent of the total population.

Essentially – is the person you want to date actually gay and/or bisexual?
There are several ways to determine this. There is Facebook stalking, first of all. Where would we be without the wonders of the internet? Especially Facebook, with those nifty little boxes for ‘relationship status’ and ‘interested in’. Special caveat for female readers: Do not trust pictures of girl-on-girl snuggles, or even kisses. For some reason, same-sex mackings are socially acceptable between girls. Huh. Imagine that.

Then there is plain old regular stalking. I do not recommend this in the literal sense. But friends, friends of friends, and some surreptitous observation can help you determine whether your target may be interested in you.

But, eventually, you will have to just man up and ask them.

There is an element of risk to this strategy. Actually, it’s just about entirely risk. There is the risk of regular rejection, and the risk of complete disgust, repulsion, and even the threat of violence. But however long you spend obsessing over their Facebook page and asking friends if they’re absolute sure, at some point, you will have to ask them out.

Popping the question.

Pro-tip: Be very clear about your intentions. I will tell you, gentle reader, the story of the first time I asked a girl out. I asked if she would like to join me for coffee. I thought I was pretty cut and dried about it. She showed up to the “date” with a couple friends, thinking that we were having a fun hang-out session. So. Make sure that if you are asking them out for coffee, you are clear that it is Coffee.
If you still aren’t sure if your potential date is straight or not, think about a disclaimer along the lines of “If you aren’t interested in me because of my gender, that is totally cool and I understand. We can still totally be friends.” Truth of the final statement may vary.

Any way you phrase it, any degree of certainty about the gayness of the participants, your proposal should be open-ended, free of pressure, and genuine.

Let’s make a date.

You got a yes! Awesome. Time to pick the venue for your date.

I actually don’t have any advice for you here. Because I’m not going on your date. You’re going on your date! And by this point you should know a lot about the person you’re going on a date with, what with all the Facebook and real-life stalking that you’ve been doing. So pick something fun, something you’ll both enjoy, something that will let you do some talking.

This next bit of advice you can feel free to ignore: take into account both your and your date’s level of comfort with being publically queer. Decide whether you will be going to a gay venue, if one is available, or a straight venue. Because, outside of small sections of big cities, if you are on a date with someone who is the same gender that you are you will be stared at. Will you go to a place with a secluded corner booth, or will you be grooving on the dance floor? That is up to the two of you.

Well, that’s it. Go forth and date.

What’s your advice for setting up a first date? How do you/have you/will you deal with determining if your potential date is, in fact, into your gender? Share your mildly embarrassing proposal stories with me!

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