You're putting the cart before the horse. Just enjoy.

mrsconn23

Dear Prudence,

I am a 50+ year-old man who just went on a date with a wonderful woman of a similar age. We had a great time, talking for several hours and she quickly agreed to a second date. I do well for myself, being an upper-middle class professional. In the course of the conversation, it became apparent that she is quite wealthy. Huge house, expensive car, friends with Senators, etc. Here’s my question: I’m thinking about our next date and future outings. I’m sure she’s been to every nice restaurant in town, many of which are probably out of my price range. I’m not quite sure how to approach picking out places and things to do that she’ll like but might be more on my financial level than hers. I certainly can aim for more personal experiences, like going for a hike or a walk in the park, but I also want our time to be special and unique. I thought, for example, about getting a docent-led tour at the art museum, but she’s on the board of the museum for Pete’s sake. I know it’s all about us getting along and that’s what really matters. Any advice in dealing with a mismatch like this in income level between partners when the less-affluent one is trying to take the lead?

—Richly in Love

charlotte989875

If she’s only in this for the fancy restaurants then is this actually something you want to pursue? I love the idea of hikes, walks, museum visits and more personal dates. Go to a bookstore or record store together. Take a cooking class. This time should be about getting to know one another to see if you’re compatible- that doesn’t require any particular spending level. 

VarunaTT

Do her a favor, don't take her out again.  This is going to be an issue for you later on and honestly, the entire letter is a red flag against you.  

The answer is do whatever TF you'd usually do for a 2nd date for someone you like.

short+sassy

Instead of always trying to "take the lead" for a date, make some suggestions and see she what she would like to do.  That can also work for restaurants.  Don't suggest any that aren't in his budget.  I've had great meals at both cheap, inexpensive places and 4-star restaurants.  I'm sure she and every other 1% has also.  Nobody wants to go to a fancy restaurant every night, even if they can afford it.

Ask her, "That's so neat you're on the board of directors at Museum!  Do you go there often?"  If she says yes, he can tell her he would love to see it with her.  She could give him an education on what they are viewing and probably love doing it, since I assume it's one of her passions.

levioosa

The insecurity is screaming here.