Wanda and Wayne,
I’ve had a crush on my best friend since high school. She helped me come out of my shell back then, and I’ve always had feelings for her. Her friends would joke about us getting married — but I was so awkward and shy back then I was just happy to have her as a great friend and didn’t want to risk losing that. We went to different colleges but stayed in touch and hung out whenever we were both home. Now that we’re back in Anchorage, we talk, text, and meet up for drinks and apps regularly.
She was recently dumped by her cheating boyfriend. He was terrible and their relationship was a disaster for more than a year. She’s still devastated and I’ve been there for her as much as she’s needed me. Seeing her so hurt breaks my heart of course but I also feel like this might finally be my chance to make a romantic move.
I’m not the scared little kid anymore. I’m confident and have dating and life experience. I know her view of me has changed as we’ve both grown up. She knows everything about my life just like I know hers. I can genuinely see us as an amazing couple. But I am worried about the timing and our friendship. How long should I wait to tell her how I feel? Should I make a move with a kiss? Be patient? I don’t want to push her but I do want to follow my heart. I know I will regret it if I don’t.
We have so much history that she could be all in with me but she might also always see me as a brother/best friend. I really don’t know how it would go. And as much as I don’t want the disappointment of being shot down by her I really don’t want to break her trust in me as a friend.
TIA for any advice.
Wanda says:
Anytime we try to move a friendship into a relationship, it’s a risk. She could shoot you down. Maybe she could brush it off and move on. Or she could feel incredibly weird after the fact and it could derail your friendship and forever fracture your vibe.
She also might feel the same way. Or perhaps she’s never let herself see you through that lens, and your declaration could trigger some curiosity and interest on her part. Maybe she’d be open to trying it out.
But whatever happens, your relationship will change. And once you tell her how you feel, how it changes is no longer up to you. You’re giving her the license to react authentically and decide the next step. For years you’ve held this secret, and in a way, secrets are empowering because you’ve always had more information than she did about the true nature of your feelings. Are you ready to give up your secret, and power, and let her decide where you go from here?
Wayne says:
I imagine this situation reads like a Ryan Reynolds rom-com script — not that I’ve burned 90 minutes of my life watching one. But here’s “The Proposal” for your “Just Friends” situation that might “Definitely, Maybe” land you love.
People always say that life is short, and in times like this someone like you would make that a mantra and dash to declare your deep love to your bestie. But here’s the thing: Life is also really, really long, and your relationship is proof.
You’ve been friends forever. Even after many years and from long distances you’ve remained tight, watched each other grow up and mature, and helped one another through life’s extreme ups and downs. You are as much family as friends.
But you aren’t brother/sister. If this is what your heart’s telling you and you want to take the shot, do it. Because you’ll certainly regret it for the rest of your hopefully long life if you don’t, and that’s a tough one to live with. If it works, congrats. If it backfires, I believe that a friendship this strong would recover from a Hail Mary kiss attempt after a good night out.
Just give it a little time first, and wait until she’s in a better space. I can’t imagine she’s ready for romance with anyone, even the soulmate that the universe has sent her. You’ll know when it’s time to make the move.
[Wayne and Wanda: Staying friends with an unrequited crush]
[Wayne and Wanda: I’m lost in the digital dating world and need to find a better way to connect]