My husband is someone you would consider “a wealthy mentor” and all he asks when we talk about it is that the kid comes prepared with questions and says thank you. Never mentioned one ordering a steak or just a burger. Don’t over think it!! He always says (so I can brag on him a bit) that he’s so thankful to give back and that people did this for him when he was younger.

He’s taken some colleagues kids to chick fil and and sat outside for an hour and some to Double Eagle. If they picked a spot that’s ’nicer’ it’s no big deal.

Here's what you do. You ask if that person has been to the restaurant before, and then ask what they're thinking about getting. Then you make sure you order something that costs either less, or no more than $5 more than them. No alcohol. No apps or desserts unless they get them too.

Nothing with spinach!

Anonymous wrote:And nothing that's difficult to eat like spaghetti or a hamburger

+1. A good approach is to eat something beforehand, then you order a reasonably priced (but non-messy) entree but you're not focused on the food because you ate beforehand. The focus should be on the conversation and mentorship, but obviously you want to eat something because it is dinner.

Order from the mid price of the menu. Follow the mentor's lead on appetizers or dessert (and drinks, if your son is old enough).

And nothing that's difficult to eat like spaghetti or a hamburger

Anonymous wrote:Ordering the most expensive item is just tacky. Shows you have no class or manners.

This. As mentioned, go over the menu and have something middle of the road picked out that he likes. This also helps when he gets there so he isn't spending time figuring out what to get.

Also, have a back up in case they don't have that item for some reason.

Ordering the most expensive item is just tacky. Shows you have no class or manners.

Anonymous wrote:Go over the menu with him and pick an entree on the more reasonable side. Not the most expensive.

Agree

Middle of the road but something he likes.

I went through this recently and just suggested my son choose something to eat which is on the cheaper side of the menu.

Go over the menu with him and pick an entree on the more reasonable side. Not the most expensive.

Ew, why mention the person is wealthy?! When someone invites you for dinner, you order whatever you want, not what they get. How weird!

He shouldn’t order light. Just regular. Not over the top.

My son asked if he should order light or just order whatever he wants. I half-jokingly said just order the same thing the mentor orders. Is that a bad idea?

I can't recall being in a one on one dinner with an older mentor at his age. When I was in college we had group dinners during internships with bosses and I just made sure not to order the most expensive. But some interns would order the most expensive and nobody cared.