Should I insist on paying for my own dinner when out with a new friend?

Do it, and good luck. It’s a tricky business paying for your own food, in these situations. He should understand. Smile and split the check.

Nah. What for? If he’s got lots of money as you say, he can pick up the bill.

Let him pay this time, then invite him out to lunch or coffee and pay. or if you are “just friends” have him over for coffee and lunch/dessert that you prepare

It is really up to you. If you are uncomfortable having him pay for your dinner, tell him so.

On the other hand, friends can and do pick up the check.

He’s already informed you that he’s buying. Let him. If you know what he likes to read, maybe take him a good book. Or like @SpatzieLover said.:)

Let him pay. Offer to cover the tip.

He invited you, let him pay. Next time you invite him and you pay for it.

If he’s already saying he’s going to buy let him buy. Maybe offer to pay next time, or tip the waiter this time.

@AmWiser You think like I do. I’m a gift giver.

If someone says “It’s my treat”, then I bring them a treat, or invite them for treats elsewhere…like saying “Instead of dessert here I know this little cafe, I’d love for you to try”

Offer but don’t push and make him feel awkward for feeling good to be able to treat you.

I think you should certainly offer to pitch in, but, don’t forget, that sometimes it is insulting to turn down a gift to the giver.

I always offer to pay for my own coffees or meal when dating, but, if my date insists I defer graciously.

Why not accept and then extend an invitation for you to cook him a nice dinner next time.

All gifts are equal, and, he’s a big boy. :-)

On another day, ask him to a matinee movie, your treat. A matinee isn’t a date.

@chyna If there’s a movie, it’s a date.

@chyna I agree anything in the afternoon is not date territory
@bob_ there’s no talking during a flick. If it’s not romantic, it’s not a date

@SpatzieLover You’d think so, but you’d be wrong.

@bob_ Day movies are not dates!

@bob_
@chyna
@SpatzieLover

But…it all depends on what content comes with said ‘not date.’
I tend to agree that a matinee is not quite a date, but, then again, if you gave the guy a ball warmer that might change the nature of ‘afternoon delight.’

If there is any touching or hand holding during said matinee it then becomes a ‘date.’

Too many variables, one must just have the experience for themselves. lol

@Coloma If one straight lady asks another out to a movie, it’s not a date.

If a straight lady asks a straight guy to a daytime movie and they’ve already established they’re “just friends”...I doubt she’d do an over the pants cock rub ;D

Let him pay this time, but say to him, “It’s not right for you to have to pay everytime we eat out, let’s say we alternate, next time lunch is on me.”

If who pays the bill is a big deal, there’s not much there, I say. Next time, you say, I“m paying.” And it’s okay to go to a cheaper place.

People get a good feeling from being able to treat a friend to a meal. Accept gracefully and assert your independence in other ways. Don’t reject the gift.

I believe in communist rules. If the other person has more money, I’m happy to let him/her pay.

But my opinion doesn’t matter—yours does. If it really bothers you to let this person pay, then by all means insist on paying your share.

Thank him, and tell him that you will pay for dessert or before or after-dinner drinks.

Can you say, “only if I can pay next time”. Or offer to cook him a meal as a thank you? If you are friends, I would feel better paying for my share when it is all counted up over the longer term.