Assess Interest in a FWB Relationship

[amofiga]

So here's my dilemma. I serve on the board of directors of my retirees association and also on the board is a woman I've known for probably 40 years and have always had a good semi-flirty relationship with her. About three years ago, she was widowed but I have no clue if she's still interested in sex. (Yes there are retirees still interested in sex.) She has her own home but spends a lot of time taking care of grand kids.

I would love to determine if she might be interested in a FWB relationship with a married man (me) but my concern is if I bring this up in the wrong way or if she is totally repulsed by the idea, it could destroy a long term working friendship and even worse, could be exposed to some of the others and basically destroy me. I can't help fantasizing about this woman and there are some things about her that lead me to believe that she can be semi-kinky.

Any clues on how to break the ice or are most of you just put off by the whole idea?

 

[TarnishedPenny]

.....

 

[Jada59]

I think you've read my FWB story. If not, read it. He just sort of starting making out with me and we took it from there. At one point, I did tell him that we would not tell others of this. He agreed. He kept his word.

That being said, we were in our 20's. I'm in my 60's and I've been told repeatedly by men that most women of my age or older, don't like sex. I believe this to be true as most of my female friends of that age do not like sex. So I don't know how far you'd get.

There's also the married thing. I would never knowingly be with a married man IRL. I was dating a guy who was married but I didn't know it. He was a coworker and I was newly hired. Our coworkers thought I knew. Nope. Found out the hard way. We didn't have sex but came close to it.

 

[NightL]

Next time she smiles at you or toward your banter, just simply say "I'd like to take you out for dinner. Would you consider that?"

You are over thinking it like a nervous teenager.

 

[amofiga]

Next time she smiles at you or toward your banter, just simply say "I'd like to take you out for dinner. Would you consider that?"

You are over thinking it like a nervous teenager.

Lunch would be the better option but you're right. Ask her to lunch and the reaction should be a good indicator. I've just thought about asking her if I could really trust her to hear me out on something without going all bonkers. If yes, then just lay it out. I'm not trying to over think but I also failed to mention that she knows my wife. I've had relationships with a fair number of married women over the years but in most cases, we both knew the score before jumping in the pool. Meeting a married woman online who is out looking herself takes away all the questions.

 

[NightL]

I also failed to mention that she knows my wife

Well if your wife is OK with you having other relationships maybe she can speak on your behalf. You could very well become a lonely old man otherwise if you stuff this up.

 

[CandK_inSE]

The whole question here is if your wife is OK with it.

If not, I'd suggest you forget all about it.

 

[amofiga]

Is my wife ok with it? There is no and there is HELL NO. If my wife were ok with it I'd have zero problem bringing it up to my friend. Yeah, unfortunately if the "friend" decided to say something to someone else who said something to another and all that chain, I could well be dead meat. Unfortunately we went through that about 16 years ago and it was ugly. Yet, I can't deny what my dirty mind keeps telling my little guy. You'd think an old fart like me would just be done with it.