First Date Finances

As I mentioned yesterday, I went on a date on Saturday, and despite both of us being quite nervous it seemed to go pretty well. In fact we're going on another one this week.

I know the generally accepted first dates are typically coffee or drinks, but ours turned into a full day adventure. We watched the Oiler's skills competition (playful hockey competition for those of you not familiar with the NHL), played several games of pool, and went for dinner.

I know it's traditional/customary for guys to pay for the first date, but I realized something this morning that has me thinking. While we were at the skills competition, he was paying for everything with cash. After we played pool, I believe he paid cash again. When we went out for dinner, he paid with a credit card. I'm well aware that it wasn't a cheap date, and I'm feeling like I should have chipped in somewhere. I don't like to think that a guy is putting himself into debt just to take me on a date!

I have a couple movie passes, so I'm covering the cost of the (much smaller) date this time. We're going during the work week, so I know this one won't turn into another 12 hour adventure. But I'm still wondering if I should have chipped in on the first one. How do you feel about first date payments? Do you go traditional, or do you believe the "he pays" is obsolete? Do you think when you switch activities that you should start chipping in? (So the first date was essentially 3 dates) I'd like to hear from you on this one.

Used

I'm conflicted at the moment.

I had an absolutely great time last night. I went for dinner with a friend at Mongoli Grill (a build your own stir fry place), then went to the season opening Oilers game (hockey for you not in the know. Battle of Alberta - Edmonton vs. Calgary, freaking awesome game). Bought a jersey, had a Starbucks & Baileys, cheered on my team to a fantastic 4-0 win and had a general good time.

... and I feel guilty.

Why? My friend makes loads more money than I do, and he paid for all of it. Well, almost. I paid for my coffee, but he probably would have paid for that too if he had been ordering at the same time. Dinner (business expense, we discussed work), game tickets (family has season tickets) and jersey (he swears it's an early Christmas gift). That's a couple hundred dollars. I know he's SUPER generous with his friends and family, has all of his debts paid off, makes 6+ figures and year and has nothing to do with it but spend it or save it... but I feel guilty accepting it. It's too much, and I don't feel like I can reciprocate. He's seeing someone, and not that kind of guy, so don't even let your mind go down that route. And please don't roll your eyes about "oh, what a terrible problem to have...". It doesn't feel good. Unless I can reciprocate it, I feel like I'm using him. I'm so much more comfortable with our usual Starbucks and farmer's market wandering.

Advice? Anyone?