Dear Bossip: I’m Secretly Diggin’ My Co-Worker

Good day, Bossip crew! We have a tricky situation that needs addressing! Take a look and leave your feedback in the thread!

Dear Bossip,

I need your advice. I met this guy at work about 2+ years ago. We exchanged numbers a became pretty good friends. Over the past years I’ve caught very STRONG feelings for this guy but I’m not sure if he feels the same. I constantly think about him 24/7 & I can’t get him out of my head, he seems to be the perfect guy. He asked me to the movies one night & made sure I had the money to pay for my own ticket. I felt like I was on cloud 9 just being with him alone that night. I’ve been to his house late at night & we feel asleep on the couch together and again I felt like I was on cloud 9. He has even mentioned us going to the beach & going out sometime but we never endup doing anything. He’s done and said a few things that makes me think that he may like me but I may be “wishful thinking’, tell me what you think. He’s suppose to be single but seems to be “good friends” with his ex-girlfriend. I bumped into them at a restaurant one evening and he introduced me as his ‘best friend” when that’s not the case. The way he did it was like he was tryna hide something. He seemed very nervous & felt that he was caught cheating & we have a platonic relationship. Do you think that was necessary? When we talk on the phone (which is not very often by the way) he asks about my relationships “so are you still with your boyfriend’ and things like that. I’m afraid to express my true feelings because I’m afraid of rejection. What should I do?

This sounds like love in the making! Tell him how you feel! You have nothing to lose and everything to gain! Rejection is a possibility whenever you pour your heart out, however, living the rest of your life wondering what would have happened if you had just told him is worse. Sometimes you have to put yourself out there. He sounds like a nice guy who wouldn’t go out of his way to be cold-hearted if you were to tell him how you feel.

The hardest part of it is, you two work together. So if he doesn’t feel the same way, you still have to see him everyday. Prepare yourself for the best and worst case scenario. But also think about whether you can handle the situation well enough that it won’t affect your job performance before you make any moves. But if you decide to, choose your time wisely – maybe a holiday weekend.

The only concern is the ex. While it is possible for people who have once dated to be friends afterwards, it can become a problem for someone else, like yourself, who ends up dating him later. Naturally, there’s a comfort zone with someone you’ve once spent so much time with, and that maybe the case with him and his ex. So since you guys talk so much and he asks you about your relationships, ask him about her before you go singing your heart song to him … preface your conversation with a “so, out of curiosity tell me about your last relationship. Why did it end? Do you still have feelings for her?” And from there you should be able to gauge if it would be wise to share your feelings.

Hope this helps! What do you think she should do, Bossip readers? Remember to e-mail all topic suggestions, feedback and questions to loveandrelationships@bossip.com!