First Date Planning

I just have to take a moment to talk about a mild annoyance of mine in regards to dating and that is when someone (in my case a guy) asks you on a FIRST date, but then expects or relies on you to plan it.

So ok, I get that the guy is trying to make sure that whatever the two of you do is something that you’ll like, but at the same time, I’m not so difficult to please that I’ll turn my nose up at any suggestion he has. To me, if we’ve talked enough to one another for the topic of going on a date to come up, I feel like at that point, he would know enough surface things about me to kind of run with an idea.

Like hey, she likes college basketball, pizza and breweries…Perhaps we could start with a a local college basketball game (relatively cheap if the team sucks) and then I can take her to this really cool brewery a few blocks away that’s known for having the best pizza in the city (yes, a place like this actually exists in my city).

BOOM. Done. Date planned.


I don’t know, maybe it’s more complex than that. Perhaps everything is these days, but I’d rather have the guy spend less time placing the owness on me (for first dates) and more time just suggesting an outing that’s to the point so we can continue to get to know one another. And yes, I have asked a guy on a date and I have suggested something for us to do based on our shared interests. And yes, the times I have done that have gone well.

Let me be clear, this mostly annoys me with FIRST dates. I’m all about sharing the planning responsibility after that date (even grabbing the tab–yes, I will grab the time from time to time). I just feel like if you’re asked out and you agree, maybe the person should have an idea of what they’d like to do WITH you?

Maybe I’m just being ungrateful, but it’s just a pet peeve of mine (or maybe I was just REALLY spoiled with that). I like it when a guy takes initiative and doesn’t allow you to stress out over coming up with something for the two of you to do. I like that he asks your preferences (or through conversation REMEMBERS things you’ve said) and takes those into consideration with planning the date. That’s hugely attractive to me.

I’ve had to “plan” 1.5 dates for this upcoming weekend. I say 1.5, because with one guy I had to literally pick the day, time and restaurant after he asked me if I was free to go out later on this week, but wanted me to put together the details so it would be, “something that I like”.




The other guy took a little more initiative and suggested we go out Saturday and framed our date activity as being a museum and dinner after, but kind of left it up to me to pick WHICH museum (we have at least a dozen in the surrounding area) and WHAT dinner place (there are too many to count in this area). I feel like we’ve spoken enough to where he could have probably gone a step further and fleshed out those details, but whatevs. I tried information gathering on his favorite types of cuisine last night via text, but all I got from that is that he doesn’t like mayo based salads (but who does?).  At least he did more than the other guy I guess. I won’t talk about the third guy, because I’m not sure if I want to go on a date with him right now.

Anyway, I suppose part of the frustration is that I dated a guy once that would NEVER make any decision as to what we did or where we would go (he would also rarely drive if it required us to take one car some place if we decided to go that route instead of meeting one another there). He would just ask for us to “get together” and that was it. And, on top of that, he had the nerve to be slightly picky. It became super annoying towards the end because I felt like he wasn’t even trying and it was exhausting to constantly plan out dates that he asked me to go on. But then on the other end of the spectrum, my ex almost always took initiative with these things (almost to a fault at times–like to itinerary levels–which could be a different kind of annoyance for another post). On our first date he literally just needed to know if I was free on a certain day and time and he ran with it. Even tossed in some “in the moment” additions to the date that worked. He actually never asked me “out” unless he had an idea of what we were doing already in  his head. Also, gotta make sure things are going well on the initial “planned” part of your date before assuming you’re about to hop around town to continue it. He should teach a class to these street urchins.

All of this rambling about dates is making sleepy and annoyed. Where is my emotional support peacock?!! I need him.


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