I have a question for you.
James and I have been best friends for 5 years. We’ve both hooked up with other people during that time and I thought I was okay with that but lately I have realized I have feelings for him. We are both not with people at the moment and went to homecoming (as friends) a couple of months ago. We had the best time but it wasn’t really a date and I don’t know if he sees me as more than a friend.
I am wondering if I should say something to him about how I feel. We’re both going to different colleges so I don’t even know if there is anything that can come of it but we have a couple months of senior year left and although I don’t want to ruin our friendship, I want to know if he feels the same way.
Do you think it’s worth a try or should I just leave it alone?
Thanks for writing in. As an adult I am going to tell you how I would handle this. But the thing is I’m 48, and literally have 30 years of living on you so the way I would handle it might seem daunting to you. Still, I’m not a fan of missed opportunity so here’s what I would do.
TELL JAMES HOW YOU FEEL: You never know the answer unless you ask the question so you could do a couple of things. You could drop hints, which according to our Good Enough Guy will basically be a waste of your time since men aren’t real great at picking those up. Or you could come right out and say it, which is what I would recommend. You don’t have to just blurt it out; I would sort of warm up to it, talking about the time you have spent together and how much it means to you and that you think you’d like to take your relationship from friendship to the next level. Word it however you want but that’s the gist of it. Once it’s out there you can deal with what’s next, which is one of two things, outright rejection or the ultimate changing of the friendship, at least temporarily.
BE PREPARED FOR REJECTION: This will be a tough pill to swallow but James might not feel the same way about you that you do about him. If that’s the case, well at least you’ll know. It doesn’t mean that it will be that way forever but it is for the time being. Now my 48-year-old self is going to let you in on a secret and again, I’m treading squarely into Good Enough Guy’s territory. Guys want to be comfortable. Even if he’s not interested now, my bet is that if you continue to be close friends, he’s going to look up one day and realize he loves you. Just my two cents.
BE PREPARED FOR THE DEATH OF YOUR FRIENDSHIP: At least temporarily. Let’s say he does decide he loves you and you begin to date. All will be great until, THE BREAK-UP. I know, I’m being a bit of a downer, I suppose it’s possible the two of you end up married and live happily ever after. But if it doesn’t go down that way, there’s gonna be a big barrier to work through to get your relationship back to where it was. That’s not to say it can’t be; I just don’t think it will be back there right away.
So that’s how I see it from my corner in Good Enough Mother World Headquarters. There’s potential here for you to be blissfully happy or suffer crushing heartache but honestly the one thing worse that the heartache is never knowing at all.
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