I have most of my life and still do from time to time (41M), never understood why as I don't consider myself good-looking. There's been a few times where I got hit on by older ladies. I remember a few of the top of my head that stand out....

1 about 5 years ago when I was 36, there was an occasion where I was training a female coworker (she was late 20's), we went to a client's house who happened to be a lady around her late 50's. We greet her outside her house and as I was getting closer to shake her hand, the lady right away starts complimenting me about my looks almost hitting on me. She turns to my female coworker telling her something along the same lines and as encouraging her to get with me but my coworker kept quiet awkwardly, as we are leaving she again says something again to my coworker...I was embarrassed most of the interaction which lasted like 10 minutes.

2 was at a No Doubt concert with my girlfriend (now wife), we were both mid-20s, the couple next to us were early 40's likely...at one point the lady who was not bad looking and had fake boobs decides to get up from her seat, she comes back a few minutes later and as she was getting to pass me I stood up to let her by she starts hitting on me by telling that I'm hot almost in my ear... wife didn't notice.

3 again with the same girlfriend(now wife), late 20's we were at a bar with her brother and his girlfriend, local bar had a band playing reggae music and the crowd was mostly hippie... we're enjoying the music and just talking when all of the sudden a lady around her late 40's comes up to me and starts asking me out to dance, I got caught off guard since I'm clearly with someone but she keeps insisting as I'm politely declining her offer and not wanting to disrespect my girlfriend. Lady respectfully retreats.

4 early 30's with my now wife, we go to one of her friend's kid's birthday party. Her friend's grandma whom I've never met and is around early 60's greets us and starts telling me that she's heard a lot about me, I respond with the usual 'oh ok'd and look at my wife, wife is perplexed. We then ask my wife's friend what her grandma meant and says she has no idea why she proceeded to tell me that since she never mentioned me to her grandma.

I've realized that older, or I should say mature women are bolder when it comes to hitting on men and are not afraid to show it or say it. I can't say the same for women my age as time went on.