It’s one of those thing I struggle with every time. Getting the first date situation, well . . . situated.

You chat along with someone, maybe transition to phone (or not) and then (yay!) decide to meet.

And then comes the choices: when, where, what to wear, etc.

I’m an equal opportunity dater – and I also hope that I’m an equal opportunity date planner. When I ask someone on a date, I usually have an activity pre-planned (get your minds out of the gutter ). So for me, I might call up and say – “Hey, I’ve got 2 tickets to this show on Friday – would you like to go with me?” or “I was thinking of going to this festival on Friday – would you like to meet there for coffee?”

But a lot of times with online dating, this doesn’t always happen.

More often it will be something like [this is not an actual, word for word conversation]:

HE: I think you are cool enough to actually meet in person. What do you think?

Me: That sounds great.

HE: Okay, so umm, uh, we should do that.

Me: We should.

HE: So what do you want to do?

Me: I’m flexible, what did you have in mind?

HE: I don’t know – what do you think?

Now, I appreciate that dating is just as nerve-wracking for guys as girls. And even in our age of equal opportunity dating, whenever you are the one doing the asking, it’s a little scary. But I just wish that we didn’t always have to dance to this song.

Because now I have to do some mind-reading tricks, and I let my membership to the psychic network expire. If I pick a place close to me, am I being selfish? If I pick a place close to you, am I starting a pattern of making things too easy? If I pick a place out of your price range, will you think me a gold digger? If I pick a place with a dollar menu, will you always think of me as your cheap date option? If I take too much control of where we go and what we do, am I emasculating you? If I offer to pay, am I emasculating you? If I don’t offer to pay and you are forced to admit you can’t afford this place, am I emasculating you? If you let me pay, are we starting a sugar momma thing? Because I am sugar-free for being the dough-re-mi donator, my friend.

If I don’t pick a place and just say, “whatever you want” am I going to send you in the same swirl of internal monologue? Am I going to frustrate you by being indecisive?

When I’m actually with someone I know well, I’ll respond back to the “where do you want to eat?” question by asking for 2-3 options. This lets them pick places they like that are in their price range and travel distance (those ankle bracelets have radiuses, y’know). But when it’s a first date, this can feel like a psychological test.

For example: We could meet at Starbucks, Golden Corral, or Texas Roadhouse.

If I pick Starbucks, that will be the cheapest option if he’s paying. But it could also signal that I don’t want to have to commit to too much time.

If I pick Golden Corral, it’s a meal. On the other hand, I’m not a big fan of mega-buffets because of my food allergies – when I try to explain that, it could make me sound like someone who is high-maintenance, potentially hypochondriac, and maybe snobby of Middle America’s ability to keep the spoon for the cornbread stuffing out of the mashed potatoes.

If I pick Texas Roadhouse, I would be very happy (love Texas Roadhouse) but then I might be at the top of his budget – because I’m a girl who likes a ribeye with mushrooms and onions and if I’m at a steakhouse, I want steak. Good steak. And I’m happy to pay for my own. But if I offer to pay, maybe I’m implying something, emasculating my date, or y’know, setting precedents. But I really like steak.

So, we do the dance, we hem and haw, and eventually we stumble to a solution that I hope passes the muster without providing a Rorshach.

Of course, I can make it work whatever happens. And reality is that this is really a first-world problem. But I have a date tonight and this is one of those things I think about as we plan the when, what, and the where.