Brandy Jensen, The Outline’s Power editor, has made a lot of mistakes in her life. Has she learned from them and become a wiser person as a result? Hahaha oh gosh no. But it does leave her uniquely qualified to tell you what not to do — because she’s probably done it.

Dear Fuck-Up,

I recently developed a pretty intense crush on a woman with whom I’m working on a project, and I feel creepy about it because this project is her vision, and I’m funding like 90 percent of it. I’m not rich, but I got some money in a settlement that I don’t really want and would feel bad living off for a couple years, so I’ve invested it in a few different things I truly believe in.

I think we have a pretty rare connection, but I’m insecure about this kind of thing. How do I express my feelings without fucking everything up? Because I don’t want this woman to think I only gave her a bunch of money to try to date her, and I don’t want her to feel gross about the project later, i.e. she revisits it later and sees my name on it and has to think about rejecting a dude who was only paying attention to her because he wanted to get in her pants. I want to be respectful and let her know that I support her art because I think she’s a good artist, and her being a good artist attracts me to her, but I’m not going to, like, pull funding or retaliate in any way if the feelings aren’t reciprocated.

To complicate shit, my wife and I are separated. So I don't want this person thinking I left my wife for her. Like a creep.

Best,
Sleepless in Seattle

Dear Sleepless,

Do not ask out this woman who is currently dependent upon your largesse. I am very dumb about art, but I cannot imagine this project will last indefinitely, and if you truly have a rare connection it will still be there once you are no longer signing checks.

Here’s where I would usually write a couple empathetic paragraphs about ethics and desire and I would probably allude to something from my past in a self-deprecating way. There’s no need for that this time though, because the answer here is simple. Keep it in your pants, Mr. de Medici.

Love,
A Fuck-Up

Have a question for A Fuck-up? Email DearFuckup@theoutline.com

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