top of page

Is He Cheap Or Just Bitter?

Cecilia asks:

Hi Christan and Sarah!

I've been dating a guy (he's 28) for the past ten months. It's my first "serious" ( or as serious as a 1 year relationship can be) relationship and overall I'm extremely happy. We communicate well for the most part, have a lot of fun, and I really care about him and enjoy being with him - he seems to feel the same. The one issue is that he is definitely a little bit of a tightwad. One of the biggest things your podcast has impressed on me is the importance of pulling my weight financially. Basically from the jump we've split costs 50/50 by taking turns paying for meals and dates, etc. However, in the past 2-3 months I'm starting to feel a little bit taken advantage of. He's not shy about asking me to kick in funds when it's his to pay and also not shy about upgrading when it's my turn- ordering dessert, more drinks than usual, suggesting a nicer place, etc. I know for a fact he makes more than me and has fewer expenses, so I don't think he's legitimately taking me for a ride, but he definitely seems pretty comfortable with this arrangement.

My issue is: how do I discuss this with him without seeming like and entitled princess (spend more money on meeee! Wahhh!)? He's made some comments in the past about how entitled he feels like many women dating can be in regards to money so I feel very sensitive about talking about it. But at the same time I'm sick of being taken out for a sub sandwich while I'm paying for surf and turf.

Help? Can you reality check me, and let me know if this is legit or if I really am being a gold digger? I've attempted to broach the topic before and he has reacted pretty defensively.

I'm going to start by saying that how you're feeling right now is how the majority of men feel when it comes to dating. So, remember this, because it's a teachable moment that you can hopefully relay to other women who insist men pay for everything.

You are not being a gold digger. Your boyfriend has a massive gaping chip on his shoulder and has decided he's going to make you pay (literally) for women that came before you. It sucks that there's a societal expectation placed on men to prove they can provide for a woman. It's an antiquated rule that far too many women still abide by and use as a measuring stick of a man's worth. Men have been paying for first, second and, like, all dates for decades. It's understandable that some of them are a little bitter.


This cheap act of his isn't cute. He is taking advantage of you. You don't want to believe that because it means he's not as great as you think he is and might have to re-evaluate the relationship.

This taking turns thing is nonsense, a strategy he cooked up to protect his own wallet. That's not how relationships work. You're not wrong or entitled or spoiled to not want to blow your paycheck on someone who clearly doesn't appreciate it.

I would approach it by first acknowledging that it sucks he's been expected to pay for everything in the past, because, let's face it, that does suck. You're experiencing right now just how demeaning it feels to be treated like an ATM. Express empathy, but follow it up with the reminder that you are not any of the women in his past and have always considered his feelings and never wanted him to feel used. Suggest that from here on out, you split everything 50/50. That way, you both have something at stake. Meaning, you're less likely to order bottle service or prime rib unless you're prepared to pay for half of it.

To be perfectly honest, I'm side-eyeing the hell out of this guy because behavior like this might hint at potential other issues down the road. He's trying to make you pay for the sins of girlfriends past, and that's just not right. I would strongly advise you assess him with a more objective eye if possible.

144 views1 comment
bottom of page