She Wants Him to Pay for Everything

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Ask A Woman: Red flag or reasonable expectation?

You're hovering a bit there bucko.

If you’ve got a question that needs the female treatment, chances are you’re not the only one who wants to ask it. Beth is our source for the answers. From opinions on men’s style to decoding the sometimes mysterious ways of women, she’ll take on a different question every Thursday. She also might provide an answer without waiting to be asked. That happens from time to time too. Click here to get to know Beth, then get in touch with her by sending your question to: .


Hi Beth:

I have started dating a really nice woman who has a home (like I do) and a good income (like I do). During a recent conversation, the topic of “who should pay” came up. While she has paid for a few of our outings in the past, she told me that she thinks a man should pay for all the things, including her upcoming vacation with him.

I don’t mind paying for a lot of things, but paying for everything? Is this a red flag that I should really be worried about?

– Brian


Hi Brian,

So this woman voluntarily paid for some of your dates together but then recently told you that she thinks the man should pay for everything? That’s confusing—no wonder you’re writing to me. I guess one explanation is that she’s dated enough in recent years that she understands the standard for most people is sharing the price of a date or switching off paying for dates at least some of the time, so she’s willing to do it to stay in the game. But personally, she thinks men should pay for everything. Maybe early on she stuck to her guns and found that it was turning off guys.

This is a red flag in that it tells you what you should expect for the future with this woman. If she tells you “I believe men should pay for everything,” she’s not going to go on paying for half or even some of your dates. I think eventually, as you get more comfortable together, as you begin to become more permanent fixtures in each other’s lives, you’ll be reaching for the check every time. I could be totally wrong. This could be a scenario where she always acknowledges that her expectations are out of line with reality…but I doubt it. Why? Because we’re talking about money. Money, more than any other topic, causes conflict in relationships. It is the number one cause of discord and parting between romantic partners. It has been my experience, too, that money habits are some of the most difficult to break. So you need to think about the future assuming that this is one of her values, and use that to evaluate how to proceed.

Mo money, mo problems. Biggie gets it.

Although I personally think this woman’s perspective is ridiculous (and outdated, hellllooooo 1985), there is nothing inherently wrong in it. People come to the table with all sorts of ideas, values, and past experiences that inform how they approach their current relationship. What causes conflict most of the time is not that one person’s beliefs are wrong, it’s that they differ from the other person’s. At which point both parties have to decide—is this a deal breaker for me or is it something I’m willing to compromise on, or surrender to entirely? And neither of those options is wrong either, because if we’re good partners, there frequently will be things we give up for the other person. So it’s simply a matter of knowing yourself. What issues are you willing to bend on, and what issues are so important to you that you refuse to move?

If you’re still feeling unclear about what to make of this woman’s stance on paying for dates, you could open up the conversation again. Ask her to clarify her position; explain why you feel the way you do; see what shakes loose. Whatever you choose to do—continue with the relationship or break it off—I think it’s most important that you simply keep your eyes open.


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