How Do You Know if He's More Than a Friend?

I'm in a crazy situation. I'm 48, and my guy friend is a very mature 27-year-old. And, I really do mean that he's incredibly mature and responsible. My husband left me a year ago, and I'm about to be divorced, now. My guy friend and I also work together very closely. He pursued me like a month after my husband left me. He really chased me down. We had not worked closely at that time, and now we do, because he asked me to work where he was and I was happy to. Here is the back-story: As soon as I changed to where he's at with work, we started hanging out together all the time. He hangs out at my house at times, we eat lunch together almost every day, and sometimes he does things like put his hand on mine when I'm trying to figure something out on the computer. For instance, my hand is on the mouse, and I will ask for help, and he'll come and put his hand on mine and try to direct the mouse. The other day in a meeting, we were sitting next to each other and we were literally arm to arm, touching, and we didn't need to be. The biggest thing to me is like 3 weeks ago, on a Saturday, he asked me if I wanted to go and eat dinner on the fly, and asked me what I felt like eating. I said Italian. He ended up taking me to this expensive, very "date-like" Italian place with a beautiful ambiance. He opened doors for me, ordered for me, and paid for me. Nothing physical has ever happened, though. Now, he is calling me his best friend. He has told me he prefers more mature women. I'm young-looking for my age and in good shape. We both have music in common. He sings, and I play the guitar. He has met my teenaged boys, and gets along with them well. We are not dating, but wow, that dinner he took me on sure felt like a date. We always sit close to each other at lunch. He always likes to make me laugh, showing me funny stuff on his phone, and I always notice that as I watch, he just sits and stares at me the entire time. Our eye-contact when we talk is really heavy and not like with any other regular person. I am SO confused! I have major feelings for him, and I don't know what I should do at this point. I get it that he's probably thinking the barriers are working together and the age-difference. I know we both acknowledge the age-difference, but I have a youthful heart and he has an older soul. Still, I'm left wondering....anything anybody can advise would be wonderful.

Has anything been said by either of you to suggest there's more than just a friendship going on here? It does sound like he likes you a lot and you do like him a lot.

No, neither of us say anything. But, I "feel" it. I don't know if that makes sense. Why would a guy who just wants to be a friend take me for an expensive dinner? And, be so chivalrous? He even opens doors for me at work. I'm not a very forward person. He is not shy, but he holds back when it comes to relationships. He's told me his dating life is a disaster. He doesn't date anyone currently, nor does he ever talk to me about other women. To be honest, we're both teachers. We teach together. We teach fourth-graders. One day, we were outside with the kids, and one of them said, "You two should get married!" This was after my guy friend told them I'm his best friend. That was the first time I ever heard him call me his best friend. It's sideways stuff like this that happens. It's never him telling me these things directily to my face. Then, the other day, he slapped one of those "slappy bracelets" (I don't know if you know what they are - those pastic things with metal that wrap around your hands) on my wrist, and the bracelet said, "Best Friends" on it. So, I just don't get him. Yet, I catch him looking at me all the time. I am thinking we're both too shy to do anything. And, I don't want to bring the subject up because I'm afraid to ruin the friendship and working relationship. But, I think about him constantly, and sometimes I just want to dump it all out on him and risk everything.

No offense but you're old enough to be his mother. How can this end well? Maybe sleep with him and get it out of your system but long term? Not likely

Good advice. The same has run through my own head.