I'm seeking older women than much of seddit, 47M here, so i don't know how much re-calibration is necessary. Just divorced at 22 years and no clue how to do anything. I am more or less on point with fitness, career and dress and am clever enough to get by. If I know people I can converse about pretty much anything. My experience with going out with women IRL who I have met online has been positive, with zero problems going from subject to subject. No fears about saying pretty much anything because we've spent some time conversing online and I feel like I have some threads to start a conversation.

But I cannot seem to crack cold opening. Once I start with some build of a compliment, I just cannot make the jump to something else, much less figure out how I could parlay it into a number or instant date.

Took a walk outside the office today and saw a set, told one that I loved her dress (I did, it was coral and fit her well), and she said thanks. We were briefly walking the same way, but I was lost for words afterwards.

Cold approached a milf @ publix and was up front, 'hi, I know this is forward, but I thought you were super cute', and immediately greeted with 'I am super married with two kids'. I mean, the rejection didn't hurt really, but did I creep her out? [She wasn't wearing a ring]

Putting in numbers is a time consuming prospect, I can go an entire day without seeing a woman worth approaching. I'm willing to do it, but what are my strategies to get a conversation going instead of

"I love X / Nice Y" "Thank you" Feels like he should have something else to say

Thanks.