Hello Dopers. I’m posting this here because the board members here are fairly intelligent and even if they’re not, at least they’re witty (some of them). And no one does any ROFLcopters or LMAOs here.
I used to work at a company as an operating manager. There were two girls who worked under me as receptionists. One of them was named Jane* and I always thought she was cute and basically my “type”. I used to call the two girls Beauty and the Beast (in front of them) as a joke because the other girl, while not ugly in any sense, was plain compared to Jane, IMO. It was never done in malice and it was a way for me to innocently express how I thought Jane was attractive. Everyone was in on this joke and no one ever took offense to it (even the Beast). I never pursued anything with Jane because at the time I was happily married and I would never cheat on my spouse. Besides, I was her manager and it would have been unethical to make any sort of move on her because of the difference in our positions. My then-wife used to come around the office sometimes so everyone at the office knew her. We’d all go out for dinner or drinks and it was a friendly work group. I quit the company about 2.5 years ago for greener pastures and haven’t kept in touch with Jane since then, or with anyone else for that matter.
Fast forward to yesterday when I received a call from Jane out of the blue. She phoned me asking me if I had kept in contact with John*. (John was from England and worked at our company for three months before he had to go back home on some family emergency.) Jane had some vacation time coming up at the beginning of December so she thought she’d take a trip to England and see if John was available to show her around. I told her that I hadn’t kept in contact with him and I wouldn’t know how to get a hold of him. We started talking some more about her upcoming vacation and I came to realize that she hadn’t made any plans at all, even though her trip was coming up in about two weeks. She hadn’t bought a flight ticket, she didn’t have any hotel reservation, she didn’t even know what the exchange rate was for the pound.
Then she started asking me about how my wife and me were doing. Although I never directly told her about our split, I thought she might have heard of it through the grapevine since they did have some common friends through the company I used to work for. I didn’t want to get into the long story about the divorce over the phone so I just gave her some cryptic answer and said “I SUPPOSE she’s doing fine”. She responded with a “oh?” but left it at that. We started talking about old times and also got caught up on recent news: she’s working at a new company, she’s moved into a new place with her father and lives half an hour away from me, she’s single and looking for things to do on the weekends. Before ending the call, I asked her if she was free for dinner sometime and we agreed to meet next Friday night.
I’ve been divorced now for about nine months and haven’t been with anybody in all that time. I’ve only recently started thinking about re-entering the dating scene, and like manna from heaven, Jane phones me up. I fancy this girl from what I remember about her from our days working together and want to see if there’s a chance for a relationship. The only thing I’m worried about is ruining this “professional” relationship we have/had. Obviously I wouldn’t mind crossing that barrier now, but I don’t know how she would feel about it. I don’t know if she just regards me as someone she can trust talking to without having him hitting on her, or as a potential romantic partner. I wouldn’t want to lose my standing with her or disappoint her by doing something inappropriate. On the other hand, I do want her to know that I find her attractive, that I’m single now, and see if there’s a chance we could do more things together in the future, gradually.
Sorry for this overly-long post, but I’d appreciate it if a third party could give me any advice on how I should handle this. I’m not afraid of rejection (I can get over that) but I don’t want to ruin the good relationship we had by betraying her trust and making the moves on her. But somehow I got the feeling (wishful thinking?) that she wants me to make a move. I’m 36 by the way and she’s 29, if that makes any difference.