Humor will not be tolerated!! -Portia

So recently I went on a "date" (I put it in quotes because he never really said it was a date but it was just us two and he paid for everything) with someone I know. It was so awkward because he kept talking about how he doesn't have enough money to do stuff (like pay for insurance and gas to drive). Then when it was time to pay, I offered to go Dutch but he insisted that he pay. Then after he was texting me and said mostly he doesn't spend money, he just splurges on dates. He's in high school though, so it's not like he has to pay rent or tuition or anything.

I don't know if this is supposed to make me feel special or something, but it doesn't. I feel awkward. Am I just being too picky or something, or is it wrong for him to talk about money and how little he has on a first date, especially after I offered to go Dutch?

Yeah, that's a huge no on his part. As in, he shouldn't be doing that.

The way I see it, there are a couple of possibilities: Either he was trying to let you know that it's a big deal that he was willing to spend money on you or he was just making conversation and picked his topic poorly. If the former, it's completely unacceptable to take a girl out and then guilt trip her for all the money you're spending on her while also insisting on paying for the date. If the latter, he's just bad at picking appropriate conversational topics (especially for a first date). Either way, his behavior was inappropriate and it's perfectly understandable that you felt awkward.

I'm glad I'm not the only one who thinks it's weird and uncomfortable and wrong.

He also told me his parents' salary. In front of his parents. Talk about awkward.

sounds like a case of being a teenager

Should've said "oh, I didn't bring my FAFSA."

One time, I was on a date with a girl and it was going kinda meh, I could tell she was pretty... immature. After a bit she started telling me how she was in huge credit card debt but that she had finally cut up all of her cards. Cool story.

Portia I actually laughed out loud at what you wrote. Very true, I should have said that xD

bismark, that sounds really lame. I just think money is definitely a subject one shouldn't bring up on the first date. Especially when it makes the other person feel guilty...

And yes, it probably is because we're teenagers too. Still annoying though :/