As much as you want to avoid admitting that you are not exactly killin’ it out there, you can only “forget” your wallet so many times before you need to fess up that there’s just… not much in there. Asking Dad for cash over drinks can help avoid that bait-and-switch feel, thereby assuaging some of your guilt over asking in the first place, and most importantly, make him more likely to say yes. You can get started on repaying him by at least getting the bill. Be classy.
You’re getting married
This is the conversation that combines all the others -- you need to know how he did it, how you can make it work, and also probably need to borrow some cash. After all the soul searching is done, though, the fun stuff begins, like picking out suits and learning how to lobby your fiancée for a chocolate fondue.