It's always awkward for me. .. I don't think it's fair for him to pay for everything but then I'll offer and I almost feel like he doesn't want to let me pay bc he's the guy and "should " pay... but I don't want him to feel resentful or burdened, especially since last night we took my 2 kids to dinner. Not sure what I should do.
It's very rare a guy feels burdened or resentful at spoiling the woman he loves. If it helps assuage your guilt, let him pay but return something in the form of surprise gifts every now and again - like a new shirt or sporting event tickets etc.
Neither of us really care for the 'the guy should pay' idea so we tend to split things where we just pay for our own thing or pay for half of the total. Sometimes one of us will pay for whatever it is but the other will always then pay next time and balance it out. It works easily like that.
In my day, the man ALWAYS paid for everything. If the woman wanted to do something, she could use her money to by some skimpy underwear or cook for him. (The cooking part works great the other way too).
Today's young men often believe the cost should be split. Many young women absolutely hate that, so they date me.
Just pay, don't bother asking him. even better do the sneaky and pretend you're going to go to the bathroom and instead go pay. I always do it with family. They always know I will when i say the word Bathroom, so i change it up a bit.. going to go get drinks, going to go outside for fresh air.. blah blah blah lol If he keeps insisting to pay (just for anything in general, be firm and say "No, it's ok, i will. It's sweet you want to pay, but let me shout you out today"
Personally i've never let a guy pay for me, for anything, outside of gifts that we both give each other. I've had guys insist they pay but that doesn't work with me. I don't like taking someone else's money, I think it makes everything awkward.