I have been dating my boyfriend for about three months and need your opinion on the appropriateness of a Valentine’s Day gift I am thinking of giving him. Part of the issue is that I have a lot more money that he does, and I think he may feel insecure about it. My attitude is if I have it, why not share it with the people I enjoy spending time with?

My gift idea is to treat him to a trip to a nice resort in Mexico. I feel like if he was doing this for me, it would be seen as socially acceptable. Since I am the one making more money as a female, he may not see it as okay, which I think is a ridiculous double-standard.

Please advise me on what to do.

Signed, Unsure Gift Giver

Dear Unsure Gift Giver,

This is an interesting dilemma. My experience has been that men say they are fine with their partners making more than they do, but deep down are still not okay with it. Also, some women are not okay with receiving elaborate gifts from their partner, just in principle. No matter what the reason, in your opinion right or wrong, if you are questioning yourself that your generous gift may not be well-received, then I would not give it to him.

I always say about gifts, it is the thought that counts– not to be embarrassed if your gift is not an equal value with what someone gives you. However, in reality, people are uncomfortable with “unequal” gift-giving and receiving.

I would discuss with your boyfriend what he is comfortable with in exchanging gifts for Valentine’s Day. I think this will avoid any awkwardness or arguments. Some couples even agree on a set dollar amount. If this is the case, then work hard to stay in the agreed upon amount, and do not try to out-do or out-shine him in the gift-giving department.