Experience of dating older woman - anyone?

LegacyUser

(not sure if correct forum, please move if not)

As the title says, anyone any experience of this?

When I say older, I mean fiftyish. I'm in my early forties.
So approximately a ten year gap.

Neither of us have children. I live alone and have been out
of the dating game for a few years, seven years now, since my last
r/ship ended.

Nothing has happened yet but there's been enough hints dropped
to know that it's something she would seriously entertain. I'm old
enough to know what innocent flirting is.

Part of me wants to go along with it, as I'm very lonely and have
suffered from shyness a lifetime. I don't there'd be anything wrong
with us having weekends away down the country, just a bit of harmless
fun.

The other part of me knows that we're quite different in terms of interests
and probably just two lonely people. I don't think the potential for a longer
relationship would be there, but that doesn't really bother me as I've been
alone so long and just crave company. She's also my line manager in work
so that's a bit of a red flag (a previous office romance ended in disaster for me
and I said never again.) I don't think i could introduce her to family and friends,
and I'd say she feels the same way.

I posted this here as I didn't want any woohoo cougar comments that i'd likely
get elsewhere. I have no friends that I'd bring this up with. I've never went out
with anyone where there was such a gap in terms of age and interest. Any advice
appreciated.

missjm

I don't there'd be anything wrong with us having weekends away down the country, just a bit of harmless fun.

don't think the potential for a longer relationship would be there, but that doesn't really bother me as I've been alone so long and just crave company. She's also my line manager in work so that's a bit of a red flag (a previous office romance ended in disaster for me
and I said never again.)

I wouldn't advise it at all based on the two quotes above. Just a bit of harmless fun with your line manager and you've already determined that there would be no future there. If you're lonely there are many other people who aren't your line manager you could hook up with. To be honest, I don't see this ending well if you were to pursue it.

LegacyUser

Reading my original post, it probably came across a bit cold. I just
honestly believe first and foremost that we'd both be looking for companionship.
I do like this lady and wouldn't mistreat or use her, we do get on very well
and enjoy good conversation and have become quite close.
I wouldn't be against the idea of something longer term, just concerned about the age and interests gap.

Stavro Mueller

So in other words you're only entertaining thoughts of this because you're lonely, single and she's there. As I read down through this I didn't think it was a good idea, then I got to the bit where you say she's your line manager. Unless you're intending to change jobs soon, you'd be insane to let this go any further. It has disaster written all over it.

Stavro Mueller

highstool wrote: »

Reading my original post, it probably came across a bit cold. I just honestly believe first and foremost that we'd both be looking for companionship.
I do like this lady and wouldn't mistreat or use her, we do get on very well
and enjoy good conversation and have become quite close.
I wouldn't be against the idea of something longer term, just concerned about the age and interests gap.

Personally I'd be more concerned about her being your line manager in work. What do you plan to do if things go tits up?

John_D80

Well for a start, I would not be too concerned about the age difference. At all. You both seem to be at the same "place" in yere lives.

Take her out a few times, casually for drinks/dinner and see how it goes. Baby steps, but just make sure she knows you are taking baby steps. As long as she always knows where she stands with you then you are doing right by her and if she wants to walk away then she can walk away. She might feel the very same as you.

Go for it and be nice to each other. Don't mess her around and everything will be fine. You might find that when you get to know her better that you want it to become something more. Ye could each be what the other needs.

daisybelle2008

highstool wrote: »

Reading my original post, it probably came across a bit cold. I just
honestly believe first and foremost that we'd both be looking for companionship.
I do like this lady and wouldn't mistreat or use her, we do get on very well
and enjoy good conversation and have become quite close.
I wouldn't be against the idea of something longer term, just concerned about the age and interests gap.

OP most people would not consider that an age gap at all. you are in your mid forties, pretty much similar middle ages, so it is hardly the cub/cougar scenario you seem to think. The interest gap shouldn't be a problem and couples with different interests can still be compatible.
The big issue is she is your boss!! Steer clear for that reason alone. Also you seem a bit socially awkward, maybe not street wise enough too know what the real problem is (it's not the age or interests!)...is there any clubs in your area or hobbies that you could take part in to meet new people and help develop more socially and combat the loneliness?

LegacyUser

Thanks for the replies. Was always going to tread carefully with
the work situation. Christmas party probably went a bit further than
both intended but as adults think we'll deal with it. To one poster,
not socially awkward, I can be shy but am involved in a few things
locally. Just haven't met anyone like this lady. Taking the xmas break
to think things through but yeah, the work thing makes this complicated
and I most likely won't pursue it. However, there's a chance I'll be moving
within the company around March time so we'll see how things are then.
I guess at xmas you're more aware of loneliness and it's easy to get
depressed.

downwesht

Go for it Op,
you only live once.
What is the point of wondering "what if"....?
You have a chance to get out of a rut and have a bit of excitement and joy in your life,grasp it with both hands.
You are both mature enough in years to deal with things if it doesn't work out, GO FOR IT!
Age is only a number