How does a guy recover from having to ask his date to pick up the cheque on a first date?

[debtfree_oneyear]

I lost my wallet, but I worry she thinks I'm either cheap or poor.

[Anonymous]

You could try explaining the situation, apologize and ask her for a second date but unfortunately with that being her first impression of you in person, it just wasn’t a good look. I know what some people would say — what’s wrong with her paying the bill? The answer is nothing, but usually the expectation is that the person who asked for the date should be the one paying for it unless there’s another understanding like splitting the bill or them offering to pay prior. I don't know when you lost your wallet but if you sprang it on her after the meal then it just looks bad man.

[petitedollbabee]

If there’s a second date, you should cover the bill since she did the first date.

[debtfree_oneyear]

But how I do get that second date?

[petitedollbabee]

You ask her out for a second date. If she enjoyed the first date then she will say yes.