Get His Info And Watch For Opportunity
I have tried to "happen" to be outside when I know I may run into him, but that hasn't worked! What, if anything, should I do?

Dear Rob,
I am a 40 yr. old, divorced single mother. A few months ago I moved into a new apartment, and there is a guy that lives in the building that I am interested in getting to know, but I have no idea how to go about it… or even if I should! ( I don’t know if he has a girlfriend, although I have never seen anyone.)

I do know he is also divorced, and he has two children. I know this because my landlord’s daughter, who is a friend of my daughters’ has talked about him to me. ( I didn’t ask! ) Apparently he is good friends with my landlord, and also works with him. I have thought about asking the landlord, or his wife something like “So, what’s Jeff’s story? Does he have a girlfriend?” But at my age that just sounds a little teenage-ish.

I have never had a conversation with him, we have said hello, and he always waves and smiles, even when he passes me on the road! I have tried to “happen” to be outside when I know I may run into him, but that hasn’t worked! What, if anything, should I do?
“A little out-of-practice”

Hi A Little Out Of Practice,
It’s fair to ask around about Jeff’s ‘situation’ before you make any moves.
This is not teenage behavior unless you stoop to the “does he like me, I like him” round-robin routine that teens do.

And I say that if he’s single, unattached, the next time go beyond saying hello to him. Ask him about his car, where he gets it repaired, you’re having trouble with yours. Something like that.
Maybe you need a quick hand getting something off a high shelf in your apartment. Something funny like changing an out of reach light bulb. You know what I mean, right?
Open the lines of communication. Don’t be afraid of making the first contact moves to get a conversation going.

After two or three of these mini-conversations if he doesn’t ask you out for a coffee, you go ahead and do it. Say to him “I could use a break, would you like to go to XXX place for coffee in half an hour?”

No matter your age, asking people in the know about someone’s personal relationship status, and I mean only asking if they are single or not, is OK to do. Just don’t get snoopy or to inquisitive.

Having the courage to initiate contact with someone is hard. Losing out on what could be a great experience or relationship is a downright shame.
Best wishes,