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Dear Veritawkward,
There’s a guy in one of my clubs who I’ve started paying more attention to, and as a result I’m developing feelings for him. The only thing (besides my overwhelming cowardice in saying something to him) is that he’s a year younger. Is this something I should pursue or should I go for a guy my own age?
Sincerely,
Robbing the Cradle?

Dear Robbing the Cradle,
Oh, honey. It’s honestly so cute that your main concern is a one-year age difference. No judgement at all, I actually find it quite adorable. As someone who has been involved with people several years younger than me, I say go for it. As long as he’s legal, of course. Sometimes younger significant others can give you that self-confidence boost you need, because obviously being older = being cooler/better/more interesting (just kidding). But seriously, one year of age difference shouldn’t come between your feelings for someone.

As for your self-proclaimed cowardice, knock that attitude off! I know it can be scary approaching someone and confessing your feelings, but I’ve always found that you regret the things you don’t do more than the things you do. Ask him to get a meal or go out for coffee after your club meets. You guys already see each other quite frequently, so it’s an easy transition to go from hanging out at club meetings to doing something one-on-one afterwards.
You got this,
Veritawkward

Dear Veritawkward,
So I’m in a bit of a sticky situation. I used to casually hook up with this one guy, but it didn’t end up going anywhere. A couple weeks ago I matched with his blockmate on Bumble and we’ve hung out a couple times. I really like this new guy and want to start getting more serious, but I’m nervous about messing with their friendship. What should I do?
Sincerely,
Blocked by a Blockmate

Dear Blocked by a Blockmate,
First of all, it’s refreshing to hear that someone at Harvard has had several hookup options, since most of us can barely find one person interested in a relationship of any kind. Congrats! However, it’s clear that the universe hasn’t totally aligned. It definitely sucks that these boys happen to be blockmates, but that’s no reason to completely drop your new bae. It’s a slight roadblock, but definitely maneuverable.

I would start by being very open with Boy #2 about your history with his blockmate, and feel out his response. If he’s chill with it, awesome! Then you can move on to step two. If not, that will be a hard pill to swallow, but you’re going to have to respect his feelings and wave the white flag. From my experience, friendship should always trump a relationship, and you definitely don’t want to ruin things between the boys.

Okay, step two: Telling Boy #1. If you guys are on good terms this should be fairly easy, and if not, just have Boy #2 talk to him. Since you said you two were never serious I doubt he’ll take it badly, but in the off-chance he does, I still stand by my advice to back off. You don’t want to get in the middle of their friendship, believe me. It’ll just end badly and lead to unfair resentments. However, I’m optimistic that it’ll all work out in your favor. Communication is the key to all good relationships, and definitely your best tool for working through this situation.
Good luck out there,
Veritawkward

—Have a burning question you want answered? Need advice on your hookups, your heartbreaks, or your significant others? Contact us at veritawkward@gmail.com.