Ex-boss flirting with me?

[Gambitgirl]

I worked for the best boss in the world for 3 years, then left his department for another job at the university for more money and benefits. While working for him I considered him a cool person and friend, in addition to a great boss. He got divorced about 2 years ago and I and several other employees/coworkers took him out to dinner/drinks to show our support b/c he was having a rough time. He's truly a very great guy and I loved working for him. After I took the new job he and I had dinner a few times and talked about work, his dating life (was married for 20 years, has no game at all now), life in general and I consider him a real friend now.

But I get the distinct impression he wants to be more than friends, based on an email he sent me a while back that said something about how the woman he was currently dating wasn't as fun as me, and something he said last night at dinner. Even though he is not my boss anymore, nor in any sort of supervisory position related to my new job, I'll probably always think of him as my boss and have that line in my mind I won't cross with him. Last night we had dinner and drinks and again I got the impression he was trying to flirt. Despite my really good opinion of him he's got a lot of things I don't want in a potential date/BF: ugly divorce, bitter ex-wife, 3 kids, dependency issues, etc.

I really love this guy to pieces AS A FRIEND and am, for the time being, just ignoring his attempts to flirt in the hopes they'll stop. I dread that he will ask me point blank soon if we can be more than friend, and I am at a loss as to how to very gently let him down, but still be firm, and not have our friendship be strained. I think he could tell I was getting a bit anxious over how the tone of the evening was with the flirting b/c he commented I seemed tense.

How to do this with the least amount of rudeness or causing any hurt feelings? Suggestions appreciated.

[Chocolate Cake]

and I am at a loss as to how to very gently let him down, but still be firm, and not have our friendship be strained.

How about, "I don't feel any chemistry beyond friendship."

[Virg]

Gambitgirl wrote:

"I dread that he will ask me point blank soon if we can be more than friend, and I am at a loss as to how to very gently let him down, but still be firm, and not have our friendship be strained."

When you find out, be sure to write it down, and you'll make millions on the book rights.  There's no easy way to do this, so honesty is the best policy.  As long as you're not mean you're not rude, and if you resign yourself to some strain in the friendship (which there will be, although possibly not permanent) you'll be able to get square with him.  Avoiding the subject is by far the best way to sour it off once you do tell him, so get it out in the open now and you'll be better off for it.

Virg

[Bijou]

I worked for the best boss in the world for 3 years, then left his department for another job at the university for more money and benefits. While working for him I considered him a cool person and friend, in addition to a great boss. He got divorced about 2 years ago and I and several other employees/coworkers took him out to dinner/drinks to show our support b/c he was having a rough time. He's truly a very great guy and I loved working for him. After I took the new job he and I had dinner a few times and talked about work, his dating life (was married for 20 years, has no game at all now), life in general and I consider him a real friend now.

But I get the distinct impression he wants to be more than friends, based on an email he sent me a while back that said something about how the woman he was currently dating wasn't as fun as me, and something he said last night at dinner. Even though he is not my boss anymore, nor in any sort of supervisory position related to my new job, I'll probably always think of him as my boss and have that line in my mind I won't cross with him. Last night we had dinner and drinks and again I got the impression he was trying to flirt. Despite my really good opinion of him he's got a lot of things I don't want in a potential date/BF: ugly divorce, bitter ex-wife, 3 kids, dependency issues, etc.

I really love this guy to pieces AS A FRIEND and am, for the time being, just ignoring his attempts to flirt in the hopes they'll stop. I dread that he will ask me point blank soon if we can be more than friend, and I am at a loss as to how to very gently let him down, but still be firm, and not have our friendship be strained. I think he could tell I was getting a bit anxious over how the tone of the evening was with the flirting b/c he commented I seemed tense.

How to do this with the least amount of rudeness or causing any hurt feelings? Suggestions appreciated.

If it were me, I would be less available for going out with him in general, and when I did, I would always include other people and make it a group thing and not a date.  If I saw someone moving in a serious direction and I were not interested, my goal would be to make it as painless as possible for them, by easing some distance into the relationship and the sooner the better.

[caranfin]

Next time he wants to get together, tell him you have a date (whether or not you're currently dating anyone).

[hkkatie]

I was also going to say you should probably stop going out to drinks/dinner with him too often by yourself. he might be taking that as a cue that you want to spend more time w/ him in an intimate atmosphere.

[supernova]

"Wow, John, this is a surprise.  I'm really flattered!  Thing is, there's actually someone else I'm sort of seeing right now, that might have potential to be the Real Thing.  I'd really like to give that a chance and see if it works out, before I start thinking about dating anyone else."

"Oh, John, you're a wonderful guy, and I'm really flattered.  I'm afraid I have a strict no-dating policy when it comes to co-workers/former co-workers/fellow students/fellow Libras/people who part their hair on the left.  I'm really sorry, because you seem like you'd be a fun date.  But if we stay just friends, we can still hang out and have fun, and that's what really matters."

"Wow.  John, you were such a good boss and mentor to me, and I can't tell you how much I appreciate and value our friendship.  But I've never really thought of you in that way.  I really don't have the ability to switch tracks like that mentally/emotionally, but I'd really like us to stay good friends."

"Goodness.  John, you've really surprised me.  I think I need some time to think about this.  You know I care for you as a good friend and I'm not sure that there's that kind of chemistry between us.  Let's just keep it at a friendly level for the time being." followed a week or so later by "John, I really think we shouldn't spend so much time together, just the two of us.  But I have this really lovely friend I'd like you to meet, she has the same hobby X as you, and maybe the three of us could..."

No, I've had no practice at this whatsoever. 

     - saphie

[alohomora]

I agree with a previous post from jeaniuskc that spending a little less time with him or hanging with him as part of a group might be a good way to go.  If he still manages to ask you out, you could maybe say something like:

"Wow. I'm very flattered that you would be interested in going out.  You know I think that you're fantastic. But I cherish our friendship far too much to ever put it at risk by dating. *pause* Also, I know that you're going through a lot right now, and I don't want to make things more complicated for you.  So if you don't feel that we can just be friends and you want to spend less time hanging out together, I respect that."