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[Standard] Don't know if I (F, 20) should pursue a romantic relationship with guy friend/co-worker (M21) bc I am feeling

My guy friend and I both like each other. Though I'd love to go out with him and be more than friends (we've only known each other for 2 months), I am worried that he might have unhidden feelings for a former crush/fellow co-worker. She's our shift supervisor and has a boyfriend. He admitted that he had a crush on her a year ago when I asked him, but she had a bf at the time. Sure, he may say that he's over her, but I have this feeling that he doesn't. If he sees her all the time at work, how can those feelings just go away? They also meet up for drinks with other co-workers after work, too. If she were to be single, wouldn't he try to pursue a romantic relationship with her then? A scarier thought is if she liked him as well.

I feel inferior compared to her, scared that I'll lose him to her and it's why I'm reluctant to risk putting myself in a situation where I might end up getting hurt. To my knowledge, he hasn't said or done anything that would be a legitimate concern. Everything is just based on isolated events (ex: he asked her for a ride home instead of asking someone else) and gut feelings. I'm intimidated by her mostly because she's physically attractive. When I asked why he liked me, he said that I was a cool gal, he liked spending time with me, and we shared a few common interests.

He has never dated before and neither have I. We're both very different people. He's an extroverted, social Aspie (though he comes across a quirky neurotypical) who gets along with everyone. I'm reserved, somewhat anti-social, and overly anxious. I don't understand what part of my personality that he likes. Yeah, we talk about his interests a lot. I may not be passionate about them, but I appreciate them and like talking to him about them. Because I have a poor image of myself, I'm very insecure and don't know if I should become romantically involved with him. I can't tell if I'm letting my insecurities cloud my judgement or ability to objectively perceive things as is.

Re: [Standard] Don't know if I (F, 20) should pursue a romantic relationship with guy friend/co-worker (M21) bc I am fee

Dating is competitive, and I understand that you're scared of rejection, but that doesn't mean you shouldn't try to get his attention. I think you should compete for him. If you never try, you'll feel much worse than if you try your best and lose out. So take a big picture view of dating, and give this your best shot. Since you've only known him for two months, give him some hints that you'd like to go out with him. Believe it or not he may be having anxiety about being rejected by you! So try to make sure to let him know you're interested by flirting and mentioning things you'd love to do -- like, you'd love to have a date for New Year's Eve! Or that you'd love to have a date to go ice skating with or to see a new movie with. Use the D (date) word so that he doesn't confuse your flirting with friendship.

And since you have some self esteem issues, face them. Don't let them win. If you feel poorly about yourself, do small things that may sound silly but that will help you feel better about yourself. Get dressed up. Read a book that he likes, so you can talk to him about it. Accentuate your best assets -- if you're funny, show him how funny you are. If you're clever, show him how clever you are. If you're a good dancer, show him a few move, fooling around. Pick one or two things you know you've got going for you, and focus on those strengths. What's most important is that you don't let your feelings about your self esteem sideline you. Life is tough, but that doesn't mean you should sit this one out. Get out there, and let him know you're looking for a date like him! ;) I hope that helps. Let me know if you need more help.
April Masini is a relationship and etiquette expert, author of 4 books and the #1 relationship advice forum, blue-chip corporate spokesperson and preferred go-to source for the world’s most prominent media and news outlets.