What I've learned at mid-life about flirting with my W....add your thoughts...with some help, maybe we'll get to a top ten list:
1) You have to be in a good place with yourself for it to really work. It has to arise from your own confidence and has to be you having fun with it. Here's where I was stuck.
2) Trying too hard ruins it. Sandi2 is right, if it isn't light-hearted and fun it's probably going to come off as creepy or clingy. For me, a lot fo the eastern philosphies (Taoism) get it right on this.
3) Once a women decides you're ok and she wants to spend some time with you, almost any attempt at flirting will be successful, almost any joke is funny. Alternatively, if she's not into you at the moment nothing you do will work.
4) I always thought that being M-ed meant really, really no flirting with anyone else. And I got quite good at recognizing and shutting down any innocent flirting right away (being a teacher makes this an important career skill). But I think I sometimes miss opportunities for my W to see that other women think I have some "value". So now I have a more balanced approach to this - I don't get involved in anything serious or anything that could become serious, but I don't worry as much about being friendly and joking around. (My W certainly doesn't!) My W has said she has never once in our 18 years together been jealous - and while that's great for her, I'm not sure it's ideal for our marriage.
5) Smile, don't let her attitude get you down.
6) There are loads of books and tips out there for "how to flirt" - heck, thanks to ebooks I've got a harddrive of em - but you'll notice that some people do these naturally, without thinking and it works. We could do the very same thing but if it is artificial or we try too hard it seems fake, creepy, or clingy. So, for me it's #1 get myself to a good place and #2 think about flirting with my W. By the time I get #1 down I usually don't have to worry as much about #2. (And, by the way, my W is NOT easy for me to flirt with; she's unusual in many ways and has a VERY low tolerance for fake, creepy, or clingy.)
PS - it would be great if your W would take up diving or something, but maybe start smaller....my W resists these sorts of things....but she'll go for an evening bike ride or hike. I think because it seems more natural. And if I plan to go with the kids, she'll sometimes say "well, can I come?" Then, added bonus, I have made the plans and know the route and W - who usually needs to be in total control - has to follow along for a little while.
