I'm a rich college kid. My friends have no idea what I want to do for them.

Dear Prudence is Slate’s advice column. Submit questions here.

Dear Prudence,

I am a young woman in college. I spent the first half of my childhood in poverty, but due to circumstances beyond my control, I ended up in my father’s custody. He is wealthy, stable, and has enjoyed a lucrative career. Consequently, he has provided me with a life of privilege: I don’t have to pay for school, he bought me a place to live, and he gives me a generous monthly allowance. Since I’m in the clear, I would like to occasionally use this wealth to help my friends.

I do try to pay for food when we all go out together (sometimes people want to split the bill), but when I hear friends of mine panicking about possibly going to part-time status (which will reduce their financial aid) because they need more money for this or that necessity, I want to help! I haven’t forgotten what it was like to have expired food in the pantry, for the power to get turned off, or worrying about getting evicted. But two issues arise out of this.

Number one: I don’t want to create a power imbalance. When people want to split the bill, I back down and split the bill because I don’t want anyone feeling indebted to me. Any gift of money I’ve ever given has been and always will be without any strings attached, but I understand that’s not an easy thing to trust. Number two: I’m ashamed to admit that I’m scared of becoming less of a friend and more of a bank. What if my friendships cease to be meaningful, and I become just a resource? One of the reasons I’m not forthright with people about my situation at the beginning is that I want a friendship to develop organically. Is there any way to offer help without jeopardizing the integrity of my friendships, one way or the other?

—Want to Pay It Forward

Dear Want to Pay It Forward,

Decide how much money you want to give away each year and set it aside with a plan to help out friends who are experiencing emergencies, however you define that. I would say dining out is not an emergency, and anything involving extended hospitalization, the sudden loss of housing, or the need to be bailed out of jail probably is. Then give generously and privately. Do it when a friend launches a crowdfunding campaign, directly asks you, or is experiencing something so catastrophic that you feel compelled to step in. Your line to them is, “I received some money from my dad that I don’t need right now, and I would love to give it to you to help you get through this time. There are no strings attached, and we never have to discuss it again.”

This frees you from the emotional drain of constantly thinking about what you should pay for and how you can get people to accept your generosity. And it avoids sending the message, “I always have more money than I know what to do with it.” Creating these guidelines for your giving avoids functioning as, or being seen as, a bank.

Plan to donate whatever is left over of that stash at the end of each year to a charity that helps people with urgent needs who aren’t lucky enough to be your friends.

Please keep questions short (

Dear Prudence,

I am lucky enough to work with three of my amazing friends. We often travel together and have been able to have some really memorable adventures. We have a huge trip planned for three months across East Asia, which has been booked and paid for, and took almost a year and a half to plan. It will include us working on some days while abroad. This schedule has been meticulously planned by us, and our managers have signed off on it since we are not missing any big deadlines or meetings.

Friend A and I have spouses, and friends B and C are engaged. All of our partners travel for work and by some miracle, we have been able to work it out so that they will be able to meet up with us for roughly 10 days of each month we are away.

The problem lies in C’s wedding planning. She has decided she must get married at the start of the third month we are away. She wants us to start cancelling things and eat the costs of non-refundable deposits and, in some cases, full payments. This has now affected our friendship. We and our partners have tried discussing things, but ultimately, it devolves into the start of an argument, and I leave. A, B, and I have no intention of going to the wedding or even attempting to salvage the friendship anymore. A and B feel we owe it to ourselves and C to have one more conversation to try and at least end on “agreeing to disagree” terms. I don’t care anymore. I have been biting my tongue and not saying what I want for a long time now. I know I can be downright evil and can say cutting things. This is why I choose to walk away from arguments. Do I just go with them one more time and hope I can bite my tongue, or let them know I really don’t think I can this time?

—Ticking Time Bomb

Dear Ticking Time Bomb,

Skip the conversations. It doesn’t sound like you have it in you to be anywhere near pleasant to C. Plus, “agree to disagree” is for opinions, not actual plans, so that doesn’t work here. I think you’re making a totally reasonable choice, but I wouldn’t expect C to feel better about the situation after a conversation. No matter how nice everyone is, you still won’t be at the wedding.

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Dear Prudence,

I was over at my brother’s place last week helping him set up a new TV in his master bedroom (he currently has a cast on one hand). After we were done, he made a dumb joke, and in response, I did a dramatic face plant on the bed. When I got up, I realized I’d left a lipstick stain on the sheet. I offered to clean it, but he told me it was no big deal, and I went home. The problem is that my sister-in-law found it and now thinks my brother is having an affair. I called her up and told her exactly what happened, but she thinks I’m lying to try to get my brother out of trouble! What can we do here?

—Lipstick Lunacy

Dear Lipstick Lunacy,

Honestly, this story sounds so contrived, I almost think you’re trying to hide your brother’s affair from me! But if it’s really true, your work is done here. You have to take comfort in the fact that it wasn’t actually your dramatic face plant that ruined their relationship. If your sister-in-law believes the worst about him, she either has good reason to or has her own issues that make it hard for her to trust him.

Classic Prudie

I am a bisexual man in my 20s. I prefer women, but I have had casual sexual relationships with men. I’m also monogamous. I am comfortable with my sexuality and realize that it’s fine to be attracted to both genders but to still have a pretty strong preference. My friends and family are also very understanding and supportive. My issue is that I have had trouble telling women I date that I am bisexual.

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I’m a rich college kid. My friends have no idea what I want to do for them.

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