Dating and money

Dear Christine,

I’ve been out to dinner three times with the same man and I really like him. He’s courteous and always insists on paying for everything. I’d like our financial obligations to be fairer, but when I offer to pay he always says no. I’m starting to feel uncomfortable and I don’t want it to color our relationship.

Financially Confused

Dear FC,

What a wonderful gentleman you are dating. His manners certainly get an “A” in my book. I also hear your predicament.

If I were talking to you in person I would ask you a little more about what you mean by “color your relationship.” Perhaps you are concerned that:

  • He is doing more than you
  • He will think you’re taking advantage
  • He will be resentful

What I know about men is – if you have offered to pay and you always say thank you after each date – then he is feeling just fine.

However, to answer your direct question – if you truly want to pay for something, I have three suggestions:

  1. If you feel very comfortable with him (you say you really like him, what do your instincts say after 3 dates?) then invite him over for a home cooked meal. The meal could either be prepared by you or the local grocery, deli, restaurant, or take-out. You supply the flowers, wine, and smiling company and he will feel completely rewarded.
  2. If you aren’t comfortable having him to your house (and don’t do it until you are completely comfortable) then when you know where you’re going for dinner, call ahead and give them your credit card and say you’ll be paying for dinner.
  3. Ask him what you could do for him that he would enjoy. Then do it. Trust me – men are much better at knowing and asking for what they want. And what he asks for will make him feel special (and you will learn more about him).

 I hope this is helpful.  Let me know.

~ Christine
Dating and Relationship Expert

Goal Setting + Purposeful Dating = Satisfying Relationships

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