Should I have let him to pay for our first date?

Dear Guys,

Last night I went on a date and had a great time with a guy. When he stepped outside to smoke a cigarette I asked for the check and paid. I suppose I did this because I had a great time and wanted to avoid the awkwardness of the bill at the end.  I think my action backfired  because when he walked back in I think he was a little embarrassed to see I had paid and protested that he would have paid.

Did I make a crucial mistake by perhaps making him feel less masculine? (Though I acted fairly quickly and without too much contemplation.) Could this have been a deal breaker?


Dear Allie,

The simple answer is no. We don’t see how this would be a deal breaker, although, that depends on the guy. If he was also having a really good time, it’s more likely he just felt embarrassed. If he wasn’t having a good time, well, then it’s an easy excuse for him not to call you again.

Let’s back up. The timing of his cigarette break is throwing us a little. Although we don’t partake ourselves, we understand that some people like a smoke at the end of a meal. It’s possible he was weighing it in his mind and decided that it was better to excuse himself for a smoke then, instead of waiting and having to smoke in front of you. Still it seems like he could have figured out a better plan, seeing it was a first date, and the bill at the end of a first date can always be a little awkward.

This is not as bad as you think. If he treats it as a deal breaker, then rest assured, he wasn’t the guy for you. That would tell you that beneath his masculine front is an insecure guy. More likely, he’ll treat this as a great opportunity to wine and dine you on a second date. On his dime of course. (Hopefully you made it clear to him that you’d like to go out on a second date.)

One thing to think about: Relationships that work out, work out because the people want them to work out. Does that make sense? Meaning, initial awkwardness is never a deal breaker when two people like each other.

Keep us posted. We hope it works out for you.



Read more Dating Advice:

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