Love, Lucy is the New School Free Press’ weekly advice column, where editors share thoughtfully researched solutions to questions about your life. Send submissions via email to nsfplovelucy@gmail.com or through Love, Lucy’s official Google Form.

“Dear Lucy, It’s a tale as old as time. I have a crush on my bff. And we’re very flirty with each other but I don’t know what to do. I couldn’t stand losing our friendship. And work is involved.” – B.P. a very enamored friend

Dearest Reader,

You’ve got yourself stuck between a rock and a hard place here, and I won’t try to sugarcoat it, this is a toughie. 

Now here’s the thing. I myself, have been on both sides of this sordid tale – at one time or another I was either the confessor or the confessee – and I must say, really neither are too pretty. 

As someone on the receiving end of a love confession, I was caught so epically off guard by the profession of love from one of my dearest, life-long friends. I felt sick to my stomach with guilt that I didn’t feel the same way, like I had done some incredible disservice to our relationship by staying on the page I was sure we were both on – until we very much weren’t. 

I was so overcome by the desire to make my friend feel loved the way they wanted to, I made out with them one night. It was messy and awkward and I regretted it almost immediately.

And then our friendship suffered for years. I know it’s dramatic, but it’s true, and if I can save just one couple of best pals from the same fate, I would sleep easier. 

As the confessor things were even harder. I engaged in a delusional, one-sided, six month courtship and eventually confessed my feelings only to be brutally rebuffed, as the great Cher Horowitz would say. Still utterly convinced I was right, I continued putting myself through different levels of purgatory until by some miracle the object of my affection actually did return the feeling. 

And although we’ll be celebrating our three-year anniversary in just two days, I’ll never forget how the first good chunk of our relationship I felt plagued by the feeling that my partner would change his mind, after all he’d already changed it once. I needed fairly constant reassurance that he still liked me, and even when I felt like I could fully trust it. Yes, things are genuinely lovely now, but that was literally just dumb luck – the imperative word there being dumb.

Now I know I’m being a bit intense but I only aim to caution you. It could work out, it really could, and some of the healthiest and most loving relationships often have their roots in strong friendships. A 2021 study suggests up to 68% of relationships start with a friends to lovers arc. Pop culture is a prime example of that – Jim and Pam, Ron and Hermione, Monica and Chandler — the examples are endless. It’s situational and definitely a case by case basis, and it could go so gloriously right. It could also crash and fucking burn. Those are some pretty risky 50/50 odds.

I don’t want to patronize you, as I can only be sure you’ve already thought through the what-ifs and found yourself either facing quite a vulnerable conversation or the thought of swallowing a feeling so big it might leave a lump in your throat for months. And I get it. The friends-to-lovers pipeline is a glorious one – if it goes to plan, that is. 

Most of the time, though, it doesn’t. I know that isn’t what you want to hear, and trust me I’d rather be telling you to hike up your big kid boots and just put it all out there, but in reality it might not be as relieving and fulfilling as you want it to be. In our twenties, we fall in and out of love faster than Lush fresh products go bad, and it can sometimes be hard to tell these fresh feelings apart. 

Falling into platonic love can be just as intoxicating as the romantic kind, sometimes even more, and it can often check boxes that other romantic relationships never have. 

And that’s wonderful. It’s precious, even, to find a person who you love so much it hurts, even though you’ve never even almost bumped uglies.

In my humble opinion, that sweet-scented kind of friendship love can be the most valuable kind, and in our tumultuous twenties, it can be even harder to find. That’s why I’m going to give you the most lame and unexciting advice there is to give: sit on it, think on it, make a pros and cons list, and let your heart ruminate for a week or two. 

It might even help to make a list of qualities about them that bother you, or that might not be ideal in a romantic partner but certainly work in a friend. Peruse through dating apps if you have them, let beautiful strangers catch your eye in public, see if that longing inside you will take the bait of anyone else. If it does, chances are good that you might just be horny – whether that be for sex or for cuddles – and not actually in love with your best friend. 

But, if you’re sure, if there’s no other possible diagnosis, and you feel like you might soon be checking into the Unrequited Love Inn. Good luck, dear reader, you might need it.

Love, Lucy <3