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Should A Younger Man Pay On A Date?


Should A Younger Man Pay On A Date?


Jerry Hall and Baptiste Giabiconi for Chanel

Dear Miss A,
I am in my fifties and have started dating a man who is 10 years younger. What is the right way to handle paying the bill after a nice dinner when he is the one who invited me? We both can afford to pay but it still makes me uncomfortable to reach for my wallet. I mentioned our age since it makes a difference. When I grew up a man paid the bill, no questions asked.

Please help me out with your advice,


Madonna and Jesus Luz

Dear Uncertain,

I think it depends on the relationship you have and the relationship you want. If you want a serious committed relationship, and not just a fling, then I think you should expect the man to pay when he invites you to lunch or dinner, especially in the beginning of a relationship. This may drive away a man who isn’t that into you, but if you are like me and see the benefit of separating the wheat from the chaff, you’ll be fine with whatever the results may be.

If you don’t see this relationship going anywhere, or don’t really want a serious relationship with someone who is your equal,  and just want him as a convenience in your life, then make it easy for him, and pay his way. Money is power. Sex is power. And of course, in Washington, power is power. Many men and some women enjoy the power that comes from being the one paying the bills for the one with whom they are in a romantic relationship. Remember that nothing is ever given for free. There is always a cost. Not to say that women or men pimp themselves out, but whether you are a prostitute, kept mistress, or a wife trapped in a gilded cage, there is often a cost you will pay.

A man who is serious about you will want to pay the bill. A man looking for the financial benefits of dating an older woman, will be happy to have you cover his costs. It’s not so much about the money, because like you said you both can afford to pay. It’s about the respect and generosity of spirit.

I’m coming from the perspective of having been raised in the South in the 1970’s and 1980’s, so I’m pretty traditional and conservative when it comes to the roles of men and women in a relationship. That said, I’m also a very independent and strong woman, so I’m a bit complicated. For me, I would want the man to pay out of respect, love and tradition, but I wouldn’t want to have to give up my power, and control. I’m not sure if that is possible.

I hope that this helps! Let me know your thoughts and how things go!

– Miss A


In 2008, I launched AskMissA.com which grew from my personal blog into a site with 700 writers, covering the intersection of charity & lifestyle in 20 U.S. cities. With Charity + Life, I am going back to a personal blog where I can share my favorite things, and continue to shine a light on nonprofits, and cause marketing campaigns to inspire others to give as they live.

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