Money, Money, Money

November 17, 2008

Dear Kirk,

My boyfriend and I have been together for six months. He is 23 and I am 48. I’m a college professor and he works at Costco as a re-stocker. I make about three times what he makes. I often end up paying for dinners out and recently paid for a weekend vacation. I want him to finish college and get a better job but he hates school and doesn’t want to do it. We are talking about him moving in to my house, so I need to set some boundaries about money and don’t know where to start. 

Dear Sugar Free Daddy,

Money is powerful, powerful stuff. I think of it like an open flame – it can be harnessed to cook your meals and keep you warm, but it can also burn the shit out of you. Anxiety about money has derailed millions of relationships.

It sounds like you guys are just getting to know each other. You’re working with a number of potent differences: age, financial status, educational background and probably a bunch of others. Tread lightly and always keep in mind what brought you together in the first place.

This is sensitive turf and it requires an enormous amount of communication. My partner and I live together. We split our bills down the middle, even though he makes more money than I do. Because of my stubborn pride and my history as a sex worker, it’s important to me that we approach our finances like this. It doesn’t always make sense, but it’s emotional for me. Early on, I asked him to never hand me money in a public place because I didn’t want people to think he was supporting me financially. So when we’re standing at an ATM machine and he hands me $20 that he owes me, I shoot him a dirty look. When we go out to dinner in a group, either I pay for both of us and he reimburses me or we contribute to the bill separately. Often enough, it’s a pain in the ass, but it’s important to me.

I’ve been in relationships, especially in my early 20s, where an older boyfriend paid for dinners, travel and theater tickets. Sometimes I would cook at home to balance this out, but sometimes we just came to an understanding that I was making a lot less money and that if he wanted to eat at a restaurant that was out of my price range, then he needed to pay for it.

Money is complicated. Our feelings about money start during childhood. Did our family have enough money to get by? Did we work as teenagers? Was there money for college? Did we ever go to school in hand-me-down clothes we got teased for? Did we get teased or feel guilty for being “rich”?

Older/younger relationships can trigger all sorts of childhood and adolescent memories and associations. The words “daddy” or “sir” or “baby” or “puppy” can send our heads spinning. That’s what makes this sort of intimacy so powerful. So it should come as no surprise that money can do the same thing, and when you mix sex and money, it can be really confusing.

Figure out a way to talk to your boyfriend about money in a way that isn’t threatening. Every now and then my boyfriend and I watch Suze Orman’s money show on PBS together. It helps us have conversations about FICO scores, investment, credit history, and debt. I should probably be struck dead for advising anyone to watch television as a way of improving their relationship, but I like Suze Orman and she helps demystify a lot of financial concepts that be completely overwhelming.

If you find yourself growing resentful about paying for things, maybe you could scale back what you do together. Maybe you go to more affordable restaurants or cook at home together or find entertainment that’s less expensive. Instead of seeing the $80 touring Broadway show, check out the $12 local performance artist. Instead of going to Cancun, go on a camping trip. Challenge the assumption that since you make differing amounts of money, the person making less is the person who should change. You are two people in a relationship making different amounts of money. Unfortunately, this isn’t as simple as finding middle ground and going out to expensive restaurants half as much. Either you, Sugar Free Daddy, eat at places that your boyfriend can afford, or you pay for it.

Cook him a nice meal! You’re bound to have a better conversation if you’re at home, with your phones turned off and you’re eating homemade food. Ask him what he hated about school. That should give you plenty to talk about.

Kirk Read can be contacted at and welcomes letters seeking advice for this blog.

Tags: Advice, Dating Tips
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I met my BF 14 years ago. At that time, he was 24 and I was in my 50's. The money and earning power difference (at that time) was even more "huge" than our age difference. However, I remember something that an old friend of mine told me when he and his much younger lover first met (they are a 35 year couple now, by the way). As long as the relationship is equal, it will work. This means, that one might have more $$ than the other and (at this point) greater earning power..but, if the other partner is strong in other ways and brings that strength to the relationship, making it a totally equal partnership, it stands a really good chance of working. However, the younger partner MUST also have a career of his own and be committed to growing it. Good luck to you both.

I have been looking for friendship with the goal ofa LTR at the end of it for a little over a year now. I haven't had casual sex in over 12 years and am disease and drug free.

My question is this.... How does one get past all the sex talk and gropes when one is looking for a life partner? It seems most guys don't really take these sites seriously. Is there something more that I can do that I haven't done to find a life partner? I have networked, joined clubs, volunteered... you name it. I don't understand why it should be so difficult to find other people who are as eager as I am to find a companion... a monogamous companion. Any tips? I just made my profile invisible out of frustration at all the offers for hook-ups and chat and phone sex.

Serious about being serious,