Afraid of Risking It All

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Dear Hoopers,
This past year, I’ve grown close to a male friend of mine who I didn’t used to think much of (we had some classes together but never spoke), but we clicked, and sure enough, I ended up falling for him. He’s very, very shy, so much of our friendship developed over texting and it’s easier for him to express himself this way. As we grew closer, he started telling me about his issues with his girlfriend. They have a long distance relationship, so there’s strain. They’ve been close to breaking up multiple times, and up until a month ago he used to tell me all about it.

Recently, his gf blocked me on instagram despite the fact that I’ve never met her before. I wasn’t sure what this meant but never told him about it as she’s now unblocked me. I’ve tried to be obvious that I like him without being too strong since he still is with his gf, even though they fight a lot. Part of me thinks maybe he suspects I like him, but our friend has said he thinks he’s oblivious. After liking him for just over 6 months now, I finally want to do something about it. I’ve told one of my friends to suggest to him that maybe the reason I haven’t told him who I like is because it’s him (this way I’m not outright confessing and disrespecting his relationship; it’s just putting the suggestion out there).

Am I doing the right thing? I’m tired of waiting for him and his gf to end their relationship. I’m also afraid to outright admit my feelings to him because I don’t want to ruin the friendship we have. I do genuinely care about him as a friend and want to see him succeed, be happy, etc. And since he’s already a shy person and is sometimes very quiet around me in person, I don’t want things to be even more awkward or weird or make him uncomfortable. At the same time, I feel like I’ve been consumed by this situation and that I’ve made nothing into something to satisfy what I really want to happen: he breaks up with his gf to be with me. I feel like I’m reaching a breaking point.
-Afraid of Risking It All

Dear Afraid,
Having known this guy for a year and developed feelings for him over time, you know that this is a legitimate feeling. You’ve been in tune with his emotions, his current relationship and developed a good friendship.

I don’t think having your friend pry is the worst idea. There is nothing wrong with putting out feelers. However, it’s second hand information. You won’t be there to see his reaction or read his body language. These can be two indicators of infatuation. Have you ever picked up on cues physically or through communication that he may be interested in you?

The biggest elephant in the room is that he has a girlfriend. And despite the fighting and catty social media behavior, he is still with her. I think it’s important to realize that rejection is probable due to him being in a present relationship.

What is more important to you; honestly sharing the feelings you have developed for him or continuing to be a friend? If you do not think remaining friends with him is possible either way due to the emotions you’ve developed, then I would say be honest and let him know how you feel. I know it may seem like you are risking it all, but if you don’t you may look back on it and wish that you had.

Dear Afraid,
What would you look back on in 5 years and regret more? Your two choices at this point are to tell him how you really feel and risk ending your friendship or waiting forever to tell him. While it is possible that they may break up someday and you can share your feelings, I’m not sure that your magical moment may ever come. Do you want to be a person that goes for it and risks failing or someone that avoids risks by sitting on the sideline?

In my life, I have had much more of a go for it approach to relationships. This has resulted in some successes and some rejections. Don’t get me wrong, those rejections were painful. But they also taught me. They helped me to figure out what I truly wanted in a relationship and helped me figure out some things about who was interested in me. Know that you certainly face risks in telling him about your feelings for him, but not telling him has risks too.
-Dr. Ryan