Crossing the line from friend to romantic partner

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.

Stop overthinking it. Just go out to dinner with her- jeez! There are definite ways that a woman lets a man know that the light is green, if you know what I mean. She will play with her hair, touch herself (not in that way, you perv), look at you and look away and look back at you, mimic your movements, lick her lips, etc, etc. If she emits emotional warmth, that’s a good sign. If she remains cool and business-associate-like, then it’s just dinner.

But it’s way too soon to be stressing like this. WAY too soon. Chill out.

Haha!

I’m sorry if I came across as being stressed.
I just wanted to know if there was a way I could tell her how I feel about her without making it look like an obvious come on.

You haven’t seen this girl in how long? How do you know you will still feel that way about her? You being available could dramatically change your relationship with this woman, how you see her and how she sees you, if the last time you related to her was when you were married and unavailable. Why don’t you go into it wondering how YOU will feel about her rather than how she will feel about you? That would take off a lot of the pressure, I think.

I haven’t seen her in person for over 2 years. But I do get photos from her in the form of cards and e-mail. And she looks better than ever!

If looks are all you’re going for here, then okay, I guess you’d still like her.

Haha.

Of course looks aren’t the only things that matter. I understand what you’re saying and I appreciate the comments.

I’m not worried about how my feelings may or may not change. I’m wondering if there’s a way to tell her how I feel without making it feel like I’ve betrayed her trust by hitting on her.

Well, let me be the first to actually offer a constructive response to your concern. You say your big concern stems from your ruining your professional relationship. You’ve both moved on in your careers, so I’m not sure why you’d see it that way. I also think that, like Alice said, you should only be asking yourself these questions after you two have actually met up. It’s natural to ask them to yourself now, but they will only be validated after the first encounter when you’ve allowed physical chemistry to enter the mix. There is no way to know what her intentions are at this point. Granted, she agreed to a rendezvous, but you won’t really know her motives until you say goodbye, and even then it may be hard to tell whether she’s as interested in you as you are in her. As far as opening your heart to her and admitting you’re crushing on her on the first date, please listen to me here. No. Absolutely not. Don’t even think about it. You will make her uncomfortable. Just play it cool and keep things as friendly as they always have been.

Let us know how it goes a week from tomorrow and maybe then we can offer opinions …

Couldn’t you just go on at least one date with her before telling her how you feel? I can’t speak for all women, but I don’t like it when a man gets too intense on the first date, even if I’ve known him for a long time first. It’s boundary-crossing, it makes me uncomfortable, and I take it as a sign that he crosses boundaries routinely. So if you ask me, you should really just chill out about it, observe her, and control your own emotions. That is taking control of the situation- not spilling your guts to her at first contact, as it were, and giving her the control. If she’s receptive to dating you, she will let you know. Trust me on this, she will.

Maybe you could say something like “I’ve always found you attractive. I’m single now. Can we do more things together in the future?”
These are things that I, as a woman out to dinner with a man I phoned, would like to hear and wouldn’t feel my trust was being betrayed by.

How was my response not constructive? As a woman who has dated both strangers and friends, I think my advice is absolutely relevant, even if you don’t agree with it. The forum is called “In My Humble Opinion”, isn’t it?

Cheers anamnesis and Alice,

I might come off sounding like a socially inept boor but I’m fairly confident with myself and I don’t intend to cause any undue pressure for me or for her. And no, I don’t plan to profess my love for her or give her the ole “I was with her but thinking of you” spiel. I guess I’ll go on the date with no expectations and see how it ends.

Wow, that’s like so… honest and upfront.

That sounds like a plan. Relax, have fun, enjoy her company, and see what happens. If you really feel curious, you could look up some information on body language. You’d be amazed how much you can tell about someone, and how they feel about you, by the way they move and hold their body. Good luck with her.

Well, I dunno, you’re a girl and I’m a guy so my constructive advice is different than yours? He needs moral support from both sides. Yeah, that’s it. :smiley:

Yeah, don’t do that either, mate. That sort of thing is not something a man should say if he wants to sound like he’s worth being with. You can be honest and upfront without coming across as being desperate for companionship or seeking her approval. Women have a built-in approval-seeking detector and they aren’t usually thrilled when it starts to go off around men.

I was never good at this. When I was a bachelor, I would go out with girls and think, “Hmm, that was a good date. Nothing spectacular though”. Later when I meet those same girls when we’re dating someone else, inevitably I get “Why didn’t you bed me that night? I gave you all the signs” and I’m like “You did?! I must have missed the part where you bared your tits at me and guided my hand towards your crotch”. For me, it’s got to be that obvious.

My wife and I were friends for a few years before we started dating. I was interested in asking her out for a long time but always worried about ruining a good friendship and kept putting it off.

Later, after we got engaged, we were talking about it and she told me that she had wished that I would ask her out since early in the friendship. She had never suggested it because she was worried about ruining a good friendship and she wasn’t sure if I even liked her that well.

My advice would be to step up and ask her out. If she’s someone that you like and think you could love, seize the opportunity before someone else does!

I don’t have any advice to give, but I have to say that I’m amazed you got away with the whole “Beauty and the Beast” thing without hurting any feelings!

  1. She made the first move. She called you.
  2. Respond by asking her out to do something casual. Pick something that gives you ample time to talk without having your attention being diverted away from each other.
  3. Be interested and interesting…as long as you are being yourself. Share the dialog; don’t hog the whole conversation, but don’t be mouse either.
  4. Be a listener AND attentive to what she is doing while she is talking…you’ll be surprised at all the cues she will be giving. Respond thoughtfully with good eye contact.
  5. The conversation will eventually turn to your current relationships. Do express the notion that it is time to seek new relationship(s) or re-establish old friendships. Don’t sound needy, but do state that you see her as either at this point in time.
  6. She’ll take it from there. Accept her response and respect it.