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(Also, I loved your letter. It made me smile and was NOT too much. Whoever told you that deserves a firm kick in the pants.)
You are definitely in a pickle! (Side note: I’m sorry for the loss of your dad!)
That said, the general principles still hold true. If Mason is interested, he’ll show you. Not always in the most obvious ways. Especially if he feels like your brother has asked him not to pursue you.
Which—why do brothers DO this? Shouldn’t they trust their most trusted friend with their sister? I don’t get it.
Anyway. Look for special things he might do for you—even small things. Especially small things.
Does he maintain eye contact? Sit close to you? Does he do little, thoughtful things?
I think the very first sign of attraction is when someone pays attention. It’s like you’re a planet and they can’t HELP but be drawn into your orbit.
So, I guess the big question is: with your brother gone, do you see Mason being drawn into your orbit?
If you’re seeing signs of ANY kind, then it might be time to step up and come clean about the attraction. But because of his relationship with your brother, I’d be super careful. The only thing worse than silently suffering with your crush is silently suffering when your crush knows and doesn’t return the feelings.
I hope that helps, and I wish you the best!
-Dr. Love
* * *
From: [email protected]
Dear Dr. Love,
AHHHHH!!! You wrote me back! Seriously, best email ever.
Ugh. Your advice though. Like, I get it. You’re totally saying all the things I already know. I sort of hoped you’d have a magic answer, but I guess that’s not a thing.
I’ll be looking for signs, though. Anything else I can do besides confessing my undying love? I’d be willing to do anything at all that would help me know without putting our friendship at risk. You know?
Anyway, thanks again for writing back and for the no-nonsense advice. I’m sure you hear this a lot, but I feel like we could be friends.
-Crushing on My Bro’s BFF
* * *
From: [email protected]
Dear Crushing,
After answering so many emails, I’ve gotten good at reading people. And I think we could be friends too.
I DO have an idea. One that might sound a little unconventional.
Sometimes people don’t realize what’s right in front of them until they’re at risk of losing it.
With that in mind … how would you feel about going on a blind date?
Your new friend,
Dr. Love
