Help! I’ve Trapped Myself in a Tortured Love Triangle of My Own Design.

Dear Prudence is Slate’s advice column. Submit questions here. (It’s anonymous!)

Dear Prudence,

Four years ago, I moved to a new city to attend grad school at a university you would certainly know. While there, I fell head over heels for one of my professors who was significantly older than me (I know, I know). I was thrilled when he asked to marry me, but devastated when he returned to his ex-wife before our marriage.

After leaving school, I found myself still living in the city, working for a friend. “Daniel” is loud, crass, and prone to sexist remarks, with a bunch of white male friends who think and act the way he does. He used to abuse alcohol but is now sober. But he is funny and has a giant heart, and helped me pick up the pieces of my life after they were shattered. I quickly fell into a physical relationship with Daniel, while he was still my boss (I know! I know!). I don’t think either of us thought it would go very far. There’s no kind way to say this, but we’re simply from different social classes and educational backgrounds. And while at times I felt we could get past that, at other times he’d flare up with some sexist crack or fall back into his womanizing ways that reminded me of why I set a mental countdown on our relationship in the first place.

Recently, while we were broken up, a third man entered my life. “Graham” is also kind, loving, highly educated, and a working professional. He also has an ex-wife. He recently broached the subject of marriage, but I find myself still thinking about Daniel (who I still work with and see every day). I suspect Daniel still carries a flame for me. And I can’t help but wonder if, with Graham, I’m repeating the first relationship that crashed down around me.

I’m thinking of accepting Graham’s proposal when it comes. On paper, I know he’s the right man for me. But I’m worried about how to handle my professional relationship with Daniel, and whether I’m picking the wrong man for all the right reasons. How do I figure this out?

–Triangle of My Own Making

Dear Triangle,

Often, jokesters submit questions to advice columns that are, in fact, synopses of books, movies, or TV shows. You know, like, “Dear Abby, I live with my four unmarried sisters in Hertfordshire and recently met a man at a party. ‘Fitz’ is a cad, haughty, and aloof! Yet I find myself unusually drawn to him …” That kind of thing. I guess they are trying to catch us out, or prove that all advice columns are bullshit, or just have a little fun.

I’m quite bad at catching these japes. But your letter smacks of a situation I’ll later kick myself for not identifying as, like, a Reese Witherspoon movie from 2009. Nevertheless, I’m answering it, because I think that the problem isn’t that this is actually fictional—it’s that you’ve chosen to view yourself as a fictional character, and it’s broken your brain. Here’s what you’ve done so far: You’ve gotten tangled up with your grad-school professor at “a university you would certainly know.” Brokenhearted when your professor returned to his wife, you moved on to dating your hot boss, though you never thought it would last because he didn’t go to a fancy university like you did. Then you met a truly nice guy, but you can’t stop worrying that maybe he’s not “the one.”

So far, so much the plot of, like, every coming-of-age story I know. You made some bad decisions, fell for some creeps, and described yourself throughout as the heroine of a quirky love story. I feel quite certain the professor’s wife does not view you as such, and neither do the co-workers who watched you immediately start hooking up with the boss. Do the professor and “Daniel” share in the blame? Sure, but you’re an adult, and you made those decisions.

Now you’ve stumbled your way into a possible happy ending and you can’t stop overdramatizing every moment. I’m glad for you that Graham is so wonderful. Yet you’re waiting for the next plot beat in your story—Will I be able to resist Daniel’s lower-middle-class charms?!—instead of merely living your life. Do everyone a favor and skip all the drama. Marry Graham, behave like a normal person around Daniel, and stop making yourself the center of the universe.

–Prudie, exasperatedly

Dear Prudence,

My best friend “Jess,” her boyfriend “Josh,” and I socialize frequently. Josh has more in common with me than with Jess, and sometimes Josh and I have organized activities together where it’s just the two of us. For example, Josh and I like to hike, meet up for coffee, go thrifting, etc. Jess is fine with this because she has a demanding schedule, and she’s happy that we are good friends.

Last week, I went to the coffee shop where we usually hang out together and the barista asked me where my “boyfriend” was (meaning Josh). This has made me evaluate how we act together. Josh has never made super romantic gestures toward me, but we have chemistry and sometimes playfully flirt with each other. When I think about all the things we have in common and how well we get along, I find myself wishing he was my boyfriend.

This is tearing me apart. Jess is my friend, but I can’t deny I’m attracted to Josh. Sometimes I feel I need to stop speaking to both of them or I’ll do something I regret, like starting a secret relationship with Josh. I know I could limit the time I spend with Josh and only hang out with him when Jess is around, but that just means I would continue falling in love with him. What do I do?

–Falling for My BFF’s Boyfriend

Dear Falling,

If this letter’s fake as well, I’m gonna guess it’s from the hit television series The O.C.
You, too, are fatally infected with Main Character Syndrome, but at least you acknowledge that the next plot point in the story you’re crafting would be bad news for everyone involved. Because there’s no sense pussyfooting around it: You definitely want to bang Josh.

And you’re too far gone for my usual advice, which would simply be, “Snap out of it!” You’re giving off vibes thick enough for baristas to observe; you’re daydreaming about Boyfriend Josh; you’re already making self-justifying statements about how actually, you have way more in common with him than his girlfriend does. You’re down bad!

So if you think you can’t control yourself around Josh, stop hanging around him. Instead, consider hanging out with poor Jess, who may not enjoy coffee, hiking, or thrifting, but surely must have something she likes to do with the person who considers herself her best friend. Spend more time with her to remind yourself of who is more important to you: the friend you love, or the guy who’s supposedly dating her but sure enjoys hanging out with her flirty, available friend.

–Prudie, reprovingly

Dear Prudence,

About a year and a half ago, I confessed that I had feelings to a close friend of mine, “Michael.” It went how I expected it to go—neither rejection nor acceptance—but it was closure for me, and I slowly but surely moved on while we both stated that we would continue to be close friends.

Still, I have good instincts, and I could tell something felt off between us. This manifested in many different ways: Quality time with my friends is important to me, and we never hung out one-on-one anymore. When Michael broke a promise to me, I was furious and acted immaturely, which I apologized profusely for. However, he failed to see his fault in the matter, and my perspective of why I was so mad (breaking trust).

The final straw (for me) was when he finally—finally—decided to have a conversation in October about “us,” he lamented a variety of things that I’ve done that made him uncomfortable, like asking him to sit with me to look at the stars. Looking at the stars was his idea, mind you.

Clearly, he’s uncomfortable around me because he still hasn’t gotten over the conversation we had a year and a half ago … which is fine, I just don’t really know what to do. I personally am done with this friendship—and I just recently got into a relationship as well—but against all logic, he still wants our friendship. I don’t do things by halves (which you can probably tell), so how do I solve this?

­–Stuck in a Bad Rom-Com

Dear Bad Rom-Com,

[looks directly at the camera like Jim in The Office]

I urge you to end this friendship immediately. It’s the kindest thing you can do for Michael—uh, and for yourself.

–Prudie, definitively

I’ve had a close male friend that I’ve been secretly in love with for years. We have almost always lived in different cities and frankly, our lifestyles are fairly different to the point that I had all but discarded the idea that we could ever be in a romantic relationship. Aside from a fun weeklong fling over a decade ago, we’ve always kept it platonic, mostly because one of us was always dating someone in the couple of times a year we’d see each other. Flash forward to this year when I told him my boyfriend and I were getting married. He seemed shocked, but happy for me, came out to help me prepare for the big day and was an all-around champ. After the wedding I talked to my new mother-in-law and was shocked to find out that he referred to me as “the one who got away” in his own life. What?