Dating a 19 year old when 44

I am a 44 year old man, recently divorced who has been getting closer to K at work, she started 4 months ago, I trained her for her first week and we have become friends at work. In one week I start in a new department doing my dream job and in 3 weeks my divorce will be absolute so I invited K out for a drink, she smiled and said
"You don't have to ask me twice to go out for a drink with you.".
Our conversations do have some sexual innuendos which I hope don't increase now and spoil things but my question is about our night out, as I have been out of the dating game so long and K is much younger than me, what do I do?
How do I continue to flirt with K and hopefully get closer without going too far a risking spoiling everything?

 

Sorry too be blunt but I wouldnt . Perhaps a reality check is needed .

Your 25 years older .

I just cant see any future in this arrangement as you will be an old man when she is still sexually active,

You need to find some one closer to your age ,

Sorry mate

 

I had a buddy that did this, he had a great time for about a year with her.

That is until he came home from work early to surprise her.

Take the Captain’s advice you will be much happier in the long run.

 

You already know this will end in a tragic fiery ball of flaming sh*t.
However... teen pussy might be worth it...

 

25 and older is reasonable, but at 19? Back off.
Just keep it to a friendship.

 

This was, if I'm honest what I was expecting. A few months, maybe more having fun together but with the knowledge in my mind that it won't be a long term thing.

 

What is she expecting - fun together until it's all over? Just be sure you both communicate what your wants and expectations are

 

Nothing wrong with that as long as he remembers this and can deal with her limits and all

 

Apart from it will probably lead to no where .

If I was single I would channel my time and energies into finding someone roughly my own age where there would be a chance of a future . That's just my view

But hey its a free world

 

But you are so wrong. Age has nothing to do. It is your mind, soul and heart that counts. Honesty and respect to make it work.

 

That's you view . I think we will agree to disagree on that one

 

Yes you can, you have to have the experience on a subject like this for an opinion. I respect your opinion. Also please, Sex got nothing to do with it.

 

Except in this case this appears to be the implied objective as below indicates.

 

Well Captain S I like to discuss with you, but I won’t because I have the utmost respect to the person I was with. In my case it was 30yrs age difference. But like most threads in here people just write what they like but have no clue about the reality. If it is an intelligent comments I can understand and I respect the comments. Some of the comments are pure ignorance and nothing else.
Captain S I wish you a happy Sunday!

 

All I really want out of this date and at least a couple of the following dates is for us both be comfortable enough to hold each other close and kiss.

 

You are 100% ready to roll homeslice.
Wear a raincoat.
Side-note if you let things end smoothly/ don't get too emotional at the end, you might end up staying fwb for many years to come.

Bon appetit

 

Can I throw something into the mix?
What if it does become a longer term thing, beyond 12 months, do relationships at our ages have a chance of lasting?

 

Do you earn 6 figures?
I mean it's working for Elon Musks dad so,,,

 

6 figures?

If you include the pence...!?

 

I suppose my thoughts today at work have returned myself to the subject of this thread, dating.

In particular upping the ante, the first kiss. Yes, I am 44 years old and have done the first kiss plenty of times but everything about this burgeoning relationship seems so different to any relationship I have had before.
We are meeting on Friday for a drink, will it be acceptable to start the evening with a simple kiss?