A gentleman or a fool?

Dear Amy: I’m a European man living in Los Angeles. I use a dating app, and the following situation has happened many times to me (as well as to other friends):

We meet at a cool wine bar at 8 p.m. Kiss on the cheek, casual conversation.

We order glasses of wine. She orders the most expensive ($23 a glass). OK.

Then she says, “Do you mind if ‘we’ order an appetizer? I’m starving.” She orders lobster bisque — the most expensive appetizer on the menu. OK.

She says, “My family comes from money … I work with them in a nonprofit.” Then she says, “I’m meeting some girlfriends for karaoke after, but I’m still hungry, so do you mind if ‘we’ order another appetizer?” OK. Then she says, “I need to use the restroom. Let’s leave after that. Can you get the bill in the meantime?” OK.

So, Amy, am I a gentleman, or a sucker?

L.A. Confused

Dear Confused: You arrived in L.A. a gentleman, and you’ve transitioned to a character in a noir movie.

I understand that there is still some cultural pressure for a man to pick up the check on a first date. The most gracious way for women to handle this awkwardness is to (of course) offer to at least split the check. Many gentlemen will respond to this offer by turning it down — which allows the man to feel both generous and appreciated.

Part of the problem might be that you are supplying a “dating” experience to someone you are meeting for the first time. But perhaps you should see your first meeting as a meeting, not a “date.”

You could shake this up by skipping the wine bars and suggesting coffee, a hike in the hills or a stroll through a farmers market. If that goes well, you can always progress to drinks/dinner later. If you invite her out, you should pick up the check.

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Dear Amy: I’m in my mid-20s, and the man in my life is seven years older. We have moved in together and love every minute we’re in each other’s presence. We have had the normal relationship talk about marriage and starting a family, and we are both on the same page.

He was once engaged, but things did not work out. A part of me thinks he is scarred from that experience. Countless times he has commented that he wants me to propose to him. It might have started as a joke, but now I believe it is what he really wants.

I have said I will never propose to him and he says, “That’s OK. Things can just stay as they are.”

I come from a family where it is believed and taught that the man is supposed to be the one to get down on bended knee, and, of course, like any little girl, I’ve dreamt of that day.

It upsets me that I am suffering the consequences of his first failed engagement. How should I handle this situation?

Wondering Woman

Dear Wondering: Yes, your guy seems to be hinting that he would like you to propose.

Even if this turns your own expectations upside down, it is something you should consider. At the very least, this is the perfect opportunity for you to initiate a serious conversation, not only about the proposal, but about marriage. Maybe you could manage a joint proposal, where you propose to each other.