Woe Is Me! is a series in which The Swaddle team indulges your pity party with advice you’ll probably ignore.

“I can’t seem to ask for my money back from friends I’ve booked flight tickets for or when I’ve paid for dinners on their behalf. These are bigger sums so I remember the times I’ve lent money, but I have problems asking for my money back even if it’s a small sum. What do I do?”

— My Two Cents

AJ: Hello, you. Asking for your money back can be quite stressful, especially when you’re friends with the person and do not intend to have awkward conversations that might purportedly jeopardize your relationship. What helps a non-confrontational person like me is to let the other person know how short I am; I highlight my own financial situation, which might encourage the other person to be a bit more empathetic. It is important to recognize the fact that you were there when your friend needed that money so badly. If it happens to be a big amount, you could make the situation a bit less stressful by suggesting they repay you in installments. For small amounts, either you let them pay next time you’re at a dinner or book a cab. I don’t think flight tickets come at a small price, so once you’ve booked them, you could just directly talk about the mode of repayment? “Hey, for the flight ticket money, does GPay work better for you or cash?”

ADT: Here’s the thing. You must strike soon and strike on payday, when people are scientifically proven to be more generous (Source: me). Sidle up to your friend, paint on the saddest face you can muster and just tell them your paycheck is late and you’re starving because you spent all your money treating your Carpal Tunnel Syndrome. (or something equally scary sounding). They’ll cough it up. Or you know, sit down with them and tell them the truth. That it makes you uncomfortable that you have to keep asking, and their lack of interest in returning the significant amount you lent them makes you feel disrespected. If that doesn’t make your account fatter, drop your friend faster than a hot potato with a spider on it and move on.

PP: You can do two things: a) “I’m sorry to ask this, but I really need that cash to pay for a pressing home renovation I need to do by the end of this month.” Don’t set the deadline too soon — you might panic them plus reduce your chances of actually getting the money. Give them a bit of notice so they can put the cash together first! or b) Play them right back. The next time you’re out in a bar or restaurant with your debtee, or are planning a trip with them, ask them to pay your share of the bill because you’re broke/forgot your wallet/misplaced your card, and since they owe you some cash anyway, would they mind paying your share? Easy!

RD: Hey! So, I struggle with this quite a bit. But it’s important to step out of your own discomfort. The other person is probably not forgetting to pay you out of malice. They might just be lazy or forgetful and know this: if and when you ask them for it, it’s probably going to make them more uncomfortable than it made you when you asked for the money back — and they will shell out. I think for me, the discomfort arises out of seeming like I’m kanjoos, or nagging, and I don’t want others to think of me this way. But for people who are close to you, it’s important to remind yourself that they would probably never see you like this, so just come right out and ask for the money. The more often you do it, the easier it will get. Holding the resentment in does no person or relationship any good. Try to normalize just asking outright, and I promise it’ll get easier.