I Insisted On Paying for Everything On Our First Date—This Is How The Guy Handled It

I’d been in the dating scene for a while and I was completely bored of having the same carbon-copy experience over and over with a guy taking me out for dinner or drinks and then never calling again. I was going to insist on paying for everything on my next date to see how he would handle it. This is what happened.

  1. It was definitely a first for me. I’d never been on a date where I was expected to pay for more than my own share, most of the time not even that. I know some friends who expect a man to pay for everything on a date, so I thought it would be interesting to see what would happen when the tables were turned. Would the guy feel like his masculinity was being threatened or would he be flattered?
  2. He was totally into it at first. I said I would head to the bar for the first round of drinks, which my date was perfectly fine with. He ordered a beer and I had a cocktail. The date started in a very pleasant way and we made some nice introductions. He talked about how he was a musician and worked in a coffee shop part-time. I also work in the creative industry, but full-time. I hoped he wouldn’t see my attempt to pay for the date as a comment on his current employment situation, but thankfully, he didn’t take it that way.
  3. Things got trickier as the night went on. I offered to pay for the next drink as my order was more expensive than his, and I rushed to the bar before he could give much of an answer. He seemed a bit bemused when I came back but again didn’t mention it. I got us the next round while he was in the bathroom and he seemed confused when he came back but didn’t say anything again, but it was clear he was starting to suspect something was up.
  4. When I went to pay for the next round, he questioned me. When I offered to go the bar again, he brought up the fact that he hadn’t paid for a drink yet (a bit awkwardly with a cute laugh). I’d been in this situation myself before when the men I date insist on paying for everything. I always feel like I have to bring it up as I don’t want to seem entitled or spoiled. My date said he felt very weird about it—he’d never experienced not having to pay for drinks on a date before. I smiled and told him not to worry about it.
  5. After I insisted on buying another drink, my date questioned me. On after I had paid for the fourth round of drinks (and we were both slightly tipsy), my date asked me why I wouldn’t let him buy a drink. I found this really interesting, as I’d never thought of asking a date why he insisted on paying for everything. I asked him if he thought it was weird. He said he did and it made him feel uncomfortable that I wouldn’t let him pay his way. I wondered why he felt so uncomfortable after me paying for four drinks when I’d let men pay for meals, drinks, and more if they insisted without really batting an eyelid.
  6. I came clean. I let my date know that I was trying a little social experiment to see how a date would react if I insisted on paying for everything. This opened up a very interesting conversation between the two of us. My date said that he felt uncomfortable as he thought I thought he was short on money due to his profession, which made him think that I might think less of him. We discussed the differences in social expectations on men and women. Basically, I’m expected to look pretty on a date and he’s expected to pay (sometimes).
  7. It made me think of dating from the guy’s side. I’d never really considered how dating can be scary and intimidating for both men and women. Men are expected to have a certain status which is closely linked to money, and they’re usually trying to impress us just as much as we are trying to impress them. While I certainly wasn’t breaking any boundaries, it still led to some interesting conversations.
  8. The date was very enlightening. I’m glad I did it and was lucky that the person I chose was smart and interested in the issues each gender faces. I also began to think twice about letting men pay for the entire date in future. I’ve never had a problem with going dutch but I’m starting to think I might actually prefer it.
Writer, reader, runner.

Marketing strategist and journalism graduate.