Every time my friend and I go out, I end up paying more than my share and feeling taken advantage of

Dear Wayne and Wanda,

“Jill” is my best friend and I really enjoy spending time together, whether it’s the movies, dinner, drinks — she’s a fun person, a great listener, the life-of-the-party type. People gravitate to her like they never have to me and when we hang out, we always have fun.

The problem is when I invite her to do something, she usually says she can’t really afford it, and I end up paying for her. Part of this is my fault — I know I’m too nice when I cave and offer to pay. But I feel like otherwise we’d never hang out.

There are other ways I feel taken advantage of too. The check will arrive and she’ll tell the waiter we’re splitting it 50-50, when I maybe had a light appetizer and salad and she had steak. She does the same thing when we settle drink tabs. Or she’ll say things like, “If you get this, I’ll get the tip” — which obviously is a lopsided arrangement. Or, “If you get this round, I’ll get the next.” Then she doesn’t.

I don’t have a lot of close friends. I work a lot, and the fact is, I can afford to pay for Jill. It isn’t breaking the bank. But I find myself wondering if she truly is broke or if she’s just cheap. I mean, she’s always dressed nice, she lives in a nice apartment, she has a decent job. Advice on how to deal with this?

Wanda says:

Let’s set Jill aside for a moment, and talk about you. My friend, you need to seriously invest in yourself — in your self-confidence, your self-worth, and especially your backbone. There’s a line between being kind and generous, and being taken advantage of, and in this situation, you crossed over long ago and remain a prisoner to your own loneliness and insecurities and your inability to stand up for yourself already. You’re letting Jill run the show — and your bank account! Enough is enough.


If you were occasionally offering to treat Jill, say on a special occasion or even just to be a nice friend, that’s fine — that’s, in fact, normal. But essentially subsidizing the social life of your friend because she either doesn’t know how to live within her means or, worse yet, is a deceitful person taking advantage of your kindness — that’s not normal! It’s dysfunctional, and it’s completely unfair to you.

No one should have to pay for friends, which is essentially what you’re doing and you’re going to have to be the one to end this cycle because Jill won’t be getting off this free ride anytime soon.

Wayne says:

Are you a side-hustle multi-millionaire? A high-profile musician, athlete or movie star? A long-lost Kardashian sister? A big-time social media influencer? Basically, are you in a financial position that allows you to easily afford having a bunch of people around you all the time simply for the sake of them telling you how amazing you are and helping you not feel alone? If so, continue on. In fact, you should grow your entourage of yes men and women. A one-person crew is just kind of, I don’t know, pedestrian.

Alas, you are simply a normal working stiff like most of us, doing good enough to put enough money in the bank to pay the rent, pump a little into the 401(k), and have some fun with friends. Thing is, Jill is doing just fine, too. And it seems she has a successful side hustle: manipulating friends into picking up tabs so she can have even more fun while keeping her cash.

While we’re all in agreement about Jill’s dodging bills skills, I’m going to present a different perspective just for fun and funds. Maybe she’s just clueless. Maybe she feels like you are always beating her in pulling out the credit card when the check arrives. Maybe she’s so in the moment of talking with you that splitting the check — her steak, your app — doesn’t even compute and seems fair and reasonable. And maybe she feels like you enjoy treating her because, well, you’re always treating her. I mean, you haven’t said anything about the situation, while she offers to help with the tips and splits.

Again, all evidence points to Jill taking advantage of your generosity and friendship. I just wanted you to thoroughly think through the situation before acting. Personally, I think the best approach moving forward is to tell your next server that you’ll have separate checks before you order, and be sure to beat her to the punch and tell her you’ll get the second round when you’re at the bar. If she’s really a friend, she’ll pony up and move on.

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at