A short letter for the holiday.
I have a friend who has feelings for this guy. He checks off all the boxes on her list, his family loves her, and they also get along super well. The issue is that her guy has never had a committed relationship before, and both of them work together, so she's afraid that if she is open with him about her feelings, it may go terribly if he doesn't really like her. She's also concerned because if he refuses her, she'll still have to see him every day at work.
Whenever they are out with friends, he makes comments about how he "wishes he had a girlfriend" and how he's doomed to be single, but she is right there in front of him, and it drives her crazy. He has issues saying no to people, and she's worried that all of the signs she has noticed from him are simply him being a good person.
Should she take the step and let him know she likes him? Or should she keep waiting on something that may never happen? She really cares for this man and can't find a good answer.
– Afraid of Rejection
You mention family, which leads me to believe that your friend and this co-worker have a strong friendship outside of the office. If that's the case, she can talk to him – outside of the office – about whether they have any romantic potential. She should say – very clearly – that she has no intention of changing how they function at work, but that she wonders about his feelings. (I write this with the assumption that they're not each other's bosses. If one of them has power over the other at work, that's another conversation.)
No matter what, disclosure is a risk. If he says he's not interested, there will be some awkwardness. But ... there's already discomfort, so their relationship shouldn't stay as it is. At the moment, it involves too much longing – and a lot of confusion – so your friend might as well ask questions and get the answers she needs.
Readers? Any thoughts on how this will work if she discloses feelings and he's not interested?