Dear Annie: I have a close friend I care about a lot, but there’s something that’s starting to get under my skin -- and I’m not sure if I should say something or let it slide. Whenever we go out -- whether it’s lunch, drinks or concerts -- we usually agree to split the cost. But somehow, I always end up paying more.
She’s “forgotten her wallet,” says she’ll Venmo me later or offers to “get the next one,” which never really happens. Most recently, we went out for dinner, and I covered the bill -- nearly $80 -- with the understanding that she’d pay me back for her half. It’s been two weeks, and despite a couple of friendly reminders, she hasn’t sent me anything.
She’s posting pictures from another night out and clearly isn’t strapped for cash. I hate to feel petty over money, but it’s starting to feel like a pattern of disrespect. Am I being too sensitive? Should I bring it up directly -- or is it better to just let it go for the sake of the friendship? -- Feeling Stuck Between Polite and Broke Dear Stuck Between Polite and Broke: You’re not being too sensitive; you’re being taken advantage of.
A real friend doesn’t repeatedly “forget” her wallet or promise to pay you back and never follow through. Once or twice might be an oversight. A consistent pattern is called freeloading.
You’ve already been more than polite. You’ve given reminders. You’ve waited.
And now you’re watching her spend money elsewhere while ignoring what she owes you. That’s not just inconsiderate; it’s disrespectful. Yes, you should say something.
You don’t have to be confrontational, just clear. Try: “Hey, I never got the $40 from dinner the other night. Can you send it this week?” If she brushes you off again or makes excuses, you’ll have your answer.
Friendship should never cost you your dignity -- or your budget. Send your questions for Annie Lane to [email protected] .
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Dear Annie: Freeloading friend never picks up her part of the tab

She's always "forgotten her wallet" or will pay via a cash app, but no money ever gets refunded for meals out.