This is a topic that has been thoroughly discussed with my friends and that doesn’t seem to get old. It’s an ongoing debate what to do with the check when at a bar, café or restaurant. I’m writing from my hetero perspective, and I have absolutely no clue how this is handled in other dating situations. But I’ve often experienced some kind of awkwardness when it comes to paying. Should the guy pay, should I offer to pay my part? I have to admit that it never crossed my mind to pay for both of us on a first date, except if I’m the one who chose the location. But I usually prefer letting the guy take the initiative. Not because I’m lazy or because I’m a greedy bitch, but because I’m looking for someone who’s assertive and invested in me. But I’m getting ahead of myself, so let’s get to the story first.

A few weeks ago, I went on a date with a guy who I’m pretty much into. Or at least, I’m pretty much into the potential thing that we could have if we start seeing each other on a regular level. So far, we’ve only hung out four times since July, and most of the time, I initiated the contact. It annoys me, but I also don’t have a problem with going for what or who I want, even though I would of course prefer being pursued from time to time instead of doing all the pursuing myself. Just for the record, I’m not harassing anyone who’s not that into me, and I’m only hitting a guy up that often before I accept that I won’t get any or not enough investment in return and leave it at that.

So when we went on a date that other day, I don’t even know how many weeks had passed since we’d last seen each other. Two at the very least, although we had both mentioned that we’re indeed both very enthusiastic about continuing to see each other. And even though I’m not thrilled about that I’m obviously not that worthy of his time, I chose to ignore this massive red flag. Besides, I have no problem being by myself, I hate most people anyway *Sagittarius rising*. Although now, it’s getting to the point where I’m almost like “whatever” when we actually hang out. And thinking about how the last date went down actually has my blood boiling.

When we were planning the date, he suggested that we go to a bar in his area, and that’s what we did. We had one round of drinks, Gin & Tonic for him, wine spritzer for me. He asked me if we should go to a different bar after, which we did, and he paid for the first round. When we arrived at the second bar (which he also chose), we had a short convo about if we’d pay by card or cash. Neither of us had much cash with us, and that was when he also mentioned that he had a rather tight budget for drinks. I think I said that I could get the second round, but then he wanted to pay by card and have me give him the cash, which was fine by me. We had the same drinks again, and I think that I should mention here that his was actually double the price of mine. However, I gave him the money for the second round as we had discussed. I actually didn’t even think about it. But where it gets really interesting is that we then stopped by a bodega where he got a third drink. (I didn’t want anything.) And I’m really confused: So he had no budget for the drinks he chose to have at the bars he knows and suggested, has me pay more than I would have actually needed to, but still needs to buy something for the road even though that would also be out of his budget???

I’m not sure if I’m overreacting here or if I’m petty, but in my opinion, if you can’t afford to take someone out barhopping, then you don’t. There are many other things that are cheap but still make a fun date. Like feeding ducks. And you especially don’t claim that you’re on a tight budget and can’t pay for an additional glass of wine, but yet have the money to get something from the bodega.

As I mentioned, I didn’t think about all this at the moment, especially because, opposed to the impression you may get from this post, I generally don’t think that much about money. I think it’s a stupid construct that humans developed to serve us, just to have us become slaves to it. So I also don’t really care who pays for what as long as things are fair. But I guess what really frustrates me in this case here is that the guy who has already shown me that he’s not overly generous with his time for me also can’t be bothered to literally invest in an evening with me, even though he clearly has the means, but rather gives me some bullshit explanation.

The worst thing is, I don’t even know if I should or would want to address it. I mean, even though highly unlikely, it could be that I’m pissed for no good reason and that it was just a miscommunication. But firstly, I’m also very non-confrontational and secondly, I don’t believe that a conversation would do much, except for me feeling stupid for arguing about money. So I guess my only option here is to see and wait how things play out in the next couple of weeks before I decide whether or not I should dump his ass.

In any case, you will get an update. In the meanwhile, I’ll be happy to read what you think about all this. Am I the overanalyzing asshole here? How do you handle money issues during the very first stages of dating?