What did I miss or am I being pranked?

[DrPope]

Short backstory is I am a semi-retired and (very) average divorced bald 59 male, tall not overweight but not a fit either. I live on the Beach in Sunny Isles Miami in my own Condo.

For about 2 years I have been going to a certain cafe for coffee and toast and sometimes lunch in a small strip mall nearby and have gotten to know the friendly owner and his staff quite well the other day I was asked by the waitress who I know well why I had never asked her out? I laughed but then the owners wife told me later she was serious and had a crush on me.
I was frankly shocked as she can't be over thirty and is a very attractive lady and I would have thought that I was way too old for her and frankly I'd never looked at her in that way and I've really only dated a few ladies recently and they were all in their 40's or 50's.

How to proceed as I have no idea what to do say and I'm very nervous about going back there.

Any opinions ?

 

[MadeleineSinha]

If you’re nervous about going back as it stands now then you have nothing to lose by asking her out for something safe, coffee, lunch, a walk in a local park.
It’s very unlikely she’s going to turn around and go ‘er, no way loser.’ Largely because neither of you are 14 and this isn’t a poor remake of Mean Girls.
Worst case, you’re uncomfortable going back now so if it doesn’t go well you’re no worse off.

 

[Escierto]

If you’re nervous about going back as it stands now then you have nothing to lose by asking her out for something safe, coffee, lunch, a walk in a local park.
It’s very unlikely she’s going to turn around and go ‘er, no way loser.’ Largely because neither of you are 14 and this isn’t a poor remake of Mean Girls.
Worst case, you’re uncomfortable going back now so if it doesn’t go well you’re no worse off.

Excellent advice and I hope he takes it.

 

[DrPope]

Someone said I should ask her why she'd never asked ME out before ... My friends all think she's one of the usual suspects but I just can't see her waiting that long if true.

 

[Spurtulator]

Someone said I should ask her why she'd never asked ME out before ... My friends all think she's one of the usual suspects but I just can't see her waiting that long if true.

What do you mean by "usual suspects"?

 

[DrPope]

Well it would be a young lady who is more interested in a man’s economic circumstances…. A common species in Miami

 

[DrPope]

Went out for coffee .... having dinner next Wednesday ..... She wants to come out on the boat on the weekend after if the weather improves

Seems to be ...well a natural progression of our friendly banter ....god help me ....

 

[Escierto]

Well it would be a young lady who is more interested in a man’s economic circumstances…. A common species in Miami

It's a common species everywhere. Most sensible women have been interested in a man's economic circumstances since the Stone Age. She wants to make sure the guy knocking her up can support their offspring.

 

[DrPope]

So umm this seems to be happening ....pinching myself really

 

[Rockymtnman]

Short backstory is I am a semi-retired and (very) average divorced bald 59 male, tall not overweight but not a fit either. I live on the Beach in Sunny Isles Miami in my own Condo.

For about 2 years I have been going to a certain cafe for coffee and toast and sometimes lunch in a small strip mall nearby and have gotten to know the friendly owner and his staff quite well the other day I was asked by the waitress who I know well why I had never asked her out? I laughed but then the owners wife told me later she was serious and had a crush on me.
I was frankly shocked as she can't be over thirty and is a very attractive lady and I would have thought that I was way too old for her and frankly I'd never looked at her in that way and I've really only dated a few ladies recently and they were all in their 40's or 50's.

How to proceed as I have no idea what to do say and I'm very nervous about going back there.

Any opinions ?

Grow a pair and ask her out?!!!! All she can say is no.

 

[DrPope]

Grow a pair and ask her out?!!!! All she can say is no.

Bit late for that now … she’s sleeping next to me as I type this

 

[Rockymtnman]

Bit late for that now … she’s sleeping next to me as I type this

Well done!!!

 

[DrPope]

Never say a 59yo man can't get on the wagon but Jesus fuck I need less Cialis .... this might be an actual romance ... and nobody is more suprised then me ...My daughter thinks I'm a Pedo dating a 34yo