Skip Nav
How Do I Prepare For a Phone Interview?
Job Search
5 Reasons You're Bombing Your Phone Interviews
Should I Buy a House?
Personal Essay
I’m a Financial Advisor — and I Rent My Home and Lease My Car
Interview Follow-Up Email Template
Job Search
Follow Up After a Job Interview With This Email

Dating Someone With More Money

Group Therapy: Dating Outside of Your Tax Bracket

This question comes from Group Therapy in our TrèsSugar Community. Add your advice in the comments!

I have recently been on a few dates with a guy who is fantastic! Our first date was nonstop conversation for four hours about everything and anything. I'm a rather shy person at first so it is incredible that I have been able to open up to this guy so readily. He has been the textbook definition of awesome so far. The only problem is that he comes from old money. I am rather middle class and have no clue how to fit into his world.

He doesn't flaunt his money at all, only contextual clues have led me to believe he is wealthy. I'm fresh out of college and struggling to have ends meet. In my past relationships I've always paid for the majority of our activities, and while it may have annoyed me at times I actually enjoyed paying for things and deciding what to do. If I can't afford to do something I simply don't do it. It's empowering. So when he wants to take me to a fancy restaurant, where I need to Google the etiquette for multiple utensil use, I freak out because I know I won't be able to afford dinner there. I never want to expect him to pay, although he has every time. He is also the type of guy who seems slightly offended by me suggesting I pick up the tab every once in a while. It feels strange because every Disney movie has told little girls this is the prince who will save you, but I feel intimidated by his ability to afford nicer things. I always expected I'd be the breadwinner in the relationship. How do I repay him or get over this? What does a girl do here?

Have a dilemma of your own? Post it, anonymously, to Group Therapy for advice, and check out what else is happening in the TrèsSugar Community.

Image Source: Thinkstock
From Our Partners
Why Do I Spend So Much Money at Target?
Makeup to Pack If You're Sleeping Over
Why You Shouldn't Stay With Your First Love
How to Take a Nude
Healthy Date Ideas
Should We Split the Cost of the Engagement Ring?
Date Ideas at Disney World
What Is iFundWomen?
Essay About Moms Selling Things on Facebook
How Much Does IVF Cost?
How Much Does a Baby Cost the First Year?
How to Save Money on Groceries When You Have Kids
From Our Partners
Latest Career & Finance
All the Latest From Ryan Reynolds