In the past few months, I met a guy, Paul, who I really have a strong connection with. I've been single for a little over a year now (I'm 20) but

In the past few months, I met a guy, Paul, who I really have a strong connection with. I’ve been single for a little over a year now (I’m 20) but I feel like it could be time to let a new love into my life. Something feels like it’s glowing up inside me when Paul is around, and the more I see him, the more I feel it.

This is really the first time since my ex that I have felt anything like that for someone, and I think it could be reciprocated, too.

I don’t know if I can say something brave to him about my feelings because - here’s the catch - he is my best friend, John’s brother. John sees me as a sister, and I really think he’d be pretty psyched to learn I could be interested in his brother. But it’s preventing me, and it could be preventing his brother, from expressing any interest in each other.

I can just feel something hanging above us when we’re together but I just don’t know where to go from here.

I’m usually super type B about a lot of things, but when it comes to love I just don’t want to miss out on something because I didn’t think it through or even worse, because I did nothing at all.

I’m looking forward to hear your input.

Thank you for everything beautiful and empowering you do.


Hello Fren,

Congratulations on your crush! It sounds like you’re all ~crushface~ all the time around this Paul and that’s a super fun feeling so, enjoy it.

My advice is very simple, which is literally just: go for it!

Based on his inevitable psyched-ness, you can keep John on a need-to-know level for the time being. Nobody is the gateway to any other person. Like, be respectful, be a good and nice friend by being mindful of his feelings, but it’s not actually up to John whether you crush on his brother or not, especially since it’s super clear that you two are just friends. Everybody is an adult, so this shouldn’t be a problem.

All’s fair in crush and war, as they say.  

If you are worried that your friendship with John will change, it’s sort of too late. You already have a crush on his brother. The dynamic of your friendship with him is currently undergoing a shift, and that’s OK! Friendships change! You are considering dating his brother, and if you make that decision, you are certainly incurring the risk that you may lose the friend, should you and Paul break up. This is certainly something to consider.

But my hunch is that you can’t, don’t want to, and probably shouldn’t put this genie back in the bottle. It sounds like you’ve already more or less made up your mind to see where this ~crushface~ feeling leads you. Life is messy! Embrace it!

I’m personally not into grand pronouncements about crushes. I don’t really think it’s necessary to approach John with a big, serious, “I have a crush on your brother. I hope that’s ok,” monologue.

I’m in favor of not making a thing out of a thing until it’s actually a thing.

I don’t think that makes flirting with Paul a “going behind John’s back” thing, I think it just gives you a little space to figure out if you two actually have viable romantic chemistry before you put it on John’s plate.

I don’t think it’s necessary to approach Paul with a big, formal confession either. That’s what flirting is for! So, be brave! Flirt! Go for it!

If I were you, I would ramp up my communication with sessi-as-hell Paul mostly via, you know, becoming more chatty on social media and working on getting a little banter-y flirtation going on “the text,” as my mom says. Make yourself a little more available, open the door for him, put yourself out there and sniff it out! If he’s into you, he’ll catch on pretty quickly and respond in kind. Flirting is fun, so have fun.

Once you’ve established more of a one-on-one rapport, ask if he wants to hang out. Keep it simple and natural. “I was thinking about seeing such and such a movie this weekend, wanna see it together?”/ “I was thinking about trying such and such an ice cream place tomorrow, wanna eat some ice cream together?”

If Paul does not show interest or curves your invitation to hang out, I think you can assume that he isn’t interested, not that he’s “worried about his brother’s feelings.”

You’re his brother’s friend, clearly, and people go to great lengths to make it happen romantically with someone they are interested in.

If this crush is mutual and meant to happen, John will probably be the last thing on his mind, and he’ll just be like, “Yes duh let’s ice cream.”

If he mentions John, you can reassure him that y’all are just friends. And if Paul’s not into it, he’s not into it.

That’s just how it goes sometimes.

Regardless, be confident in your own agency as you navigate this situation. There’s nothing wrong with centering your own needs and desires. And be mindful of the fact that family dynamics are weird and unpredictable; if you end up sensing that something weird is going on between John and Paul, it probably has almost nothing to do with you.

Keep your focus on being honest, compassionate and kind. And let their relationship be their relationship.

If you do end up making plans to hang out with Paul, I would give John the heads up in a sensitive way that stops short of asking his permission to go through with the plans. Don’t make a massive deal about it, but tell him you’ve been crushing on his brother and the two of you are planning to hang out and that you’re really excited! Yay! It’s OK if that feels a little bit awkward. Just embrace the awkwardness.

If flirting with Paul is a dead end, you can either just leave it in the past, or you can confess to John that you had a little unrequited crush on his bro and the two of you can laugh about it together. That’s what BFFs are for.

If for some reason any of this causes John to have a jealous meltdown, the two of you are going to have to have an honest conversation about your friendship which might be difficult, but the truth will be better for each of you in the long run.

Write and let me know what happens!!

Xoxoxo

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