Dating a 19 year old when 44

Like friendly /on the cheek maybe?
I'd focus more on trying to feel out how she responds to being in close quarters with you.
Like maybe after drinks find something else to do, order a subcompact Uber so you'll be a bit crowded and just see, does she do everything in her power to stick to her side of the car or is she comfortable enough with you to make the best of things and snuggle a bit.

 

In my view you should kiss only on the cheek when you first meet. Normally the right cheek and sometimes both in parts of Europe. Its a gesture of friendship. .

 

But it won't be a first meet as we have been chatting most days since middle of February, I think I will lean in for a kiss and see how she responds.

 

I dont mean a first meet as in a very first occasion /daye

I mean its used as a greeting as you you would shake hands in business .

I would leave the proper kiss until the end after you have dropped her off or escorted her to a waiting taxi . You never know she could invite you in for a coffee so be prepared

 

In nearly every relationship I have had we have had sex within the first week but this is one thing I really want to wait for with K, the thought of having sex with K hasn't crossed my mind at all.

 

Maybe she sees you as a father figure.

 

She has joked about this with me a few times and a friend at work has described K as 'wet behind the ears' so you could be right.

On a serious note, how should I behave when I am with her? Obviously our first date will be a getting to know each other better date but after this, what should I do to help reinforce my father figure status to her?

 

Treat her with respect and take an interest in her .A lot of guys on first dates fall into the trap of just talking about themselves all night . Compliment her on her appearance. Dont forget she will be as nervous as you are .and so the more at ease she feels the better things will be.

 

How can I bring this question up in general conversation without making things awkward, or at least minimising the awkwardness?

 

I think given the flirtatious nature of previous dialog you are overthinking it all and risk choking up with indecision or general anxiety

Just take a deep breath and go out for drinks and enjoy that time together, try and be the same guy you were last week & just roll with it as it plays out, by 44 I'd hope you were able to tell when a young lady is fawning over you in a social setting.
Be more concerned towards the end ofthe evening, when wrapping up drinks does she seem eager to get home or maybe up for some windowshopping / casual stroll in some mall or just anything to prolong the evening.

 

Thanks @FritzDaKatx2

I am really worried about overthinking things because this is something that has plagued me in the 2 relationships I have had in the 12 months since the breakdown of my controlling marriage. I will naturally try and be the same guy I am was last week and hopefully the evening will just flow
Being able to tell when a lady is fawning over me might be a small problem. I have noticed how K's behaviour towards me has changed and become more affectionate over the last few weeks but I just hope I don't panic and move in for our first proper kiss too soon.

 

It is not happening!
I have blocked her on Facebook and Messenger and now I have moved departments and will be working completely different shifts I won't see her again.

 

Oh I am sorry.
You will find someone.

 

I think you’re better off. Mature women have so much more to offer. Enjoy the pursuit!

 

Young may look good, but many times there is excess baggage. You may have made right move, but you'll regret later, always wondering what could have been.

 

Yes, I realise this is a very likely outcome but if I was ton start a relationship with K there are many more ways in which it could go wrong and cost me in the much longer run.

 

I am sorry things didnt work out .

I just feel energies and time would be better channeled into someone more compatible and similar age. Relationships can work with partners of vastly different ages but they are relatively rare.

You sound like a gentleman to me and as such there will be someone out there waiting for you .

 

I don't know if it is sensible of me or not but me and K have been talking

 

I'm someone who has been into older guys her entire life, and 25 is too large of a gap in my mind. I see how this could fall apart badly. There is unlikely to be a long-term future in a relations with such a large gap.

 

Nothing wrong with that . You can be very good friends even close friends . I have always had a very close female friend. Someone who I can talk to about delicate things . She supported me and advised me when my Mrs went through the change .