I'm a modern woman, but I still believe there is something chivalrous about the man paying for the first couple of dates. I've heard some men say they feel offended when the woman offers to pay, and others are offended when she doesn't. Often I will at least do "the reach" for the wallet, which feels insincere, but then I feel guilty when I don't. And if the man does pay for the first dates, at which point should that change? I don't want to seem like a princess or a gold digger. Is there a right way to handle who should pay?
I don't think you seem like a princess or a gold digger if you prefer your date to treat you the first few times you go out. Not that long ago the man was always expected to be the one who paid. Of course courtship was a completely formal affair then, and gender roles more rigid. The flexibility and freedom we enjoy today means there's more choice, but with that choice comes ambiguity, mixed signals and stress.
To like a dash of traditional gender roles in the beginning of your relationships is not a bad thing. It's just something you like, the same way you might like guys with curly hair or who love dogs. If you're on a date with someone who insists on splitting things equally, then yes, the moment the check arrives might feel awkward. But it might also feel awkward if tells you he's into the NRA and you're more NPR. Not every date is going to be a perfect match.
Instead of thinking about what is right or wrong in terms of who "should" pay, think of the dance of the dinner check as an opportunity to pick up three important clues about your compatibility.
Our financial behavior is a subtle but important form of communication. Let's take "the reach," for example. You worry that the reach is insincere. In fact this move tells the exact truth about your preferences. You'd like him to pay (if you truly wanted to split it you'd reach for the check, not your wallet) but you don't want to obligate him. It invites him to signal back that yes, he's okay with that; "Please, it's my treat," or that he has a different preference; "Thanks. Your half is $36." On the surface this exchange is just about a financial transaction, but really it's a mini presentation of who you are and the type of relationship you like.
When a man pays for a date, you interpret that as an expression of chivalry. Someone else might think it's an expression of chauvinism. Dating is a search for someone who will be the yin to our yang. Just because a date might want to split the check doesn't necessarily rule him out as a potential partner, but it tells you something about who he is and what he likes, and you can determine if that works for you.
The trickiest part of your question is when to transition from him always taking you out to a more equal arrangement. In your single life you are probably empowered and independent, and you want be seen that way in your relationships, too, hence your concern about seeming like a princess. If date number two goes well and it seems like this guy might have a future, you can suggest, "Next one's on me." This tells him that you may like a traditional set-up when things are casual, but as it gets serious you expect to be an equal partner. If he is rigid about it and refuses to ever let you pay, it could be a sign that he's not okay with that.
I know it can be uncomfortable, but those awkward moments reveal a lot. Learning to decode financial behavior can actually help in your search for a good match.
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