Let's see assuming I were on an outing that's been established as a date (which I do not consider an automatic thing just because the person I'm doing said outing with happens to be male). I would expect mutality, prefer generosity, and expect him to keep unpleasant financial surprises to a minimum. So if we're going to a movie or play or other event and he expects me to pay for my ticket, that should be stated at the time of invitation as well as the cost; it shouldn't be sprung on me on the way there. If he's paying for me he just needs to say not to worry about the money. If I'm driving and have to pay for gas and parking, it would be nice for him to balance that out some way and vice versa ( Example: with one friend (not a date, just a good example of balance) she drove us both and paid for parking so I picked up her dinner after the play). Also I think if you're the invitee, it's also just good manners to offer and be prepared to pay your share.
I'll also say that while it might be nice to have someone spend massive amounts of money on me to give me a wonderful evening, it might also hinder his long term chances (especially if done frequently) because part of the long term happiness of a couple would be dependent on how they handle their finances together and so I'm evaluating how he manages and values his money.
If this gets too complicated, my fallback plan is to become a rich old maid and spend my money visiting all my CC singles forum friends.
What would you say if you (a single working mom) were engaged to a man (with adult children) and he often let you pay for coffee, dinner, and outings? Or he conveniently forgets his wallet? When my oldest daughters were dating, their boyfriend/fiance would fill up their gas tanks if they drove to meet them, would slip money into their purses if they made a home-cooked meal for the two of them and would NEVER allow them to pay for a thing.
Assuming that I'm understanding the situation right: he's not contributing at all to your finances or the financial needs of your children (and the children are young enough that they need caring for); he's planning to marry you and become part of your household; he's still making you pay for yourself and often for him out of your already tight budget (I'm assuming this is a normal situation, not a multi-millionaire actress dating a delivery guy type of financial disparity). I'd say, what the crap am I doing engaged to this guy? I just can't imagine that a guy who acts that selfish with his money that far into a relationship is going to be any sort of advantage or blessing to have in your life. Marrying him will be like adding another child to the family only he'll be even less likely to be respectful and co-operative than a well raised child.