50s how to signal my interest or read the signs of my friend

[relationshipnc]

NC for this but asking for some gentle (please) advice... divorced, building back my life in midlife. I lack confidence/recent experience after a long marriage, with dating, making the move, showing interest. I have a male friend who I've occasionally seen for drinks over the past year, post divorce and we share an interest where we meet up occasionally to pursue. He's always really responsive, suggesting things to do and utterly courteous and gentlemanly. He's divorced too. I do like him, but I'm not sure how to signal I'd like to move onto a more romantic relationship, or read that he might be interested in that. I'm struggling to read his sign. Anyone being in the same position? Any tips? I don't want to mess up the friendship but have feelings for him.

Bump

I would ramp up the contact you have and see if he responds in an enthusiastic way.
If he does, do some flirting

I think the usual advice given is if he's interested you would know and while that is likely, he could be shy or just a bit haphazard about things.

I think I might wait for a pause after a moment of shared laughter and comment airily that I was reflecting the other day and thinking that I would quite like to see if I could share my life with someone special again. Perhaps then say, "You always seem so independent and fulfilled. I don't suppose you ever feel like that, do you?" with a genuine question inflection. If he's interested but doesn't respond to that I'm not sure how to help.

maybe he is feeling the same, but is the same as you and doesn’t want to mess up the relationship either,
light flirting, touch his arm a bit , say something nice to him

If he is up for meeting socially, can you just start to increase the amount of times you do this - if he is enthusiastic about meeting two or three times a week, or at weekends, then you will get to know each other well and things might start to happen.