• Relationships

Dear Wendy: “When Should I Tell Him I Have Feelings For Him?”

For the past few months, I’ve been developing a friendship with a guy named Kevin. I felt some kind of a connection with him from the beginning, and that has continued to grow the more we spend time together. I didn’t really put much thought into our connection, however, because he had a girlfriend he seemed pretty crazy about and I considered him off-limits. But that all changed when his girlfriend suddenly moved cross-country last weekend for family reasons, presumably for good. They are no longer technically together. As soon as she left, all the feelings that I had been trying to suppress hit me like a ton of bricks. I realized how much I like Kevin and how much I could see myself with him, even though I’d been trying to deny it when he was taken. Now he’s all I can think about, but he’s still distraught over his sudden break-up, and its a messy situation because they broke up for such circumstantial reasons. I know he feels something for me too, but the timing is so bad, and I feel like I can’t just wait when I can’t even stop thinking about him for more than two seconds in succession. Should I tell him my feelings now, wait for a while, or just forget it altogether? When will I know that it’s right, or that I should just give up? — Can’t Deny My Feelings

If it’s been less than a week since Kevin’s girlfriend suddenly left town, at least give him a couple more weeks to process his feelings. Unloading on him now will not only mess up his healing process, it will confuse whatever feelings he might have growing for you. It could be easy for Kevin to simply transfer the love he felt/feels for his very recent ex onto you, especially as there’s a sudden void in his life now you could easily fill, but do you really want to be a stand-in for his ex? No, you want to be liked for you, right? So, give Kevin a little time. Let the shock wear off. Let him deal with feeling hurt and angry. Continue being his friend and you’ll get a sense when he’s starting to move on a little. And when you sense an opening, let him know that you care about him and you have feelings for him, and if there’s a chance he could feel something similar for you, you’d love to pursue a relationship with him once he feels emotionally ready to be with someone else.

I’ve known my friend for about two years. We’re in college and have pretty much been joined at the hip since freshman orientation. The thing is, I’ve really liked him for the entire time I’ve known him. The longer I waited to tell him how I felt the more nervous I got about doing so. He’s a really great friend and I’m worried about losing him. Recently, he told me that he wants to transfer to another college as soon as next semester. This school is very far away, not even within any sort of driving distance. Now that it looks like our days might be numbered, I’m just wondering if I should just suck it up and tell him how I feel and, if it goes well, how to make a decent transition out of the friend zone. Should I even try or just enjoy our friendship for what it is? — The Friend

Sure, tell him. If he’s moving far away, what do you really have to lose at this point? Besides, he hasn’t said for sure he’s transferring to another school — or that he’s even been accepted yet; it sounds like he simply “wants” to transfer. Maybe your confession will change his plans; maybe not. The best thing you can do is expect that your revelation won’t change anything and he’ll move as planned. If his new school isn’t even driving distance away from where you are now, it would probably be very difficult to maintain a long-distance relationship. More difficult hurdles have been jumped, of course, but you should probably prepare yourself for the likelihood of nothing coming from sharing your feelings except the relief of finally getting it off your chest and saving yourself from wondering forever “what could have happened” if you’d only been open. And that, TF, is certainly worth spilling the beans.

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*If you have a relationship/dating question I can help answer, send me your letters at {encode=”dearwendy@thefrisky.com” title=”dearwendy@thefrisky.com”}.

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