My first date in... 32 years; I won't lie, it's a bit odd

I wouldn't overthink it. I wouldn't consider it an official date, even though it probably is. She could have sent just a thank you card if that's all she wanted to do, and a month later? I'd say that is a pretty strong indication of a date, but play it cool in your head if it's getting awkward.

Thank you folks, I appreciate you taking the time to reply.
It is psychologically weird nothing else, she is in her mid-fifties, about 10 years younger than me (note to self-must update my age on my profile).
Yes, I have been overthinking it, something I have always been prone to, perhaps because I spend so much time alone. Fortunately, the time invested in reflecting on my marriage has been useful and I do have a clear idea of what I do / don't want. As you say Angeleyes65 we are older, wiser and better for it.
Thanks folks, I agree with your analysis I'll pop along and see how it goes.
Still the last time I met up with a woman like this was, literally, half my lifetime ago. Even just saying it in my head feels weird.
I'll keep you posted.

Exciting stuff. I'm putting a placeholder here to share some of my dating tips when I have a few minutes if its of any assistance to you at all.

Ok Here we go. Mostly common sense but always good to refresh

Grooming
Dress to impress but in context. If you have a sister, daughter, friend who has good fashion sense, enlist their help on wardrobe decisions. Shave, hair is tidy. Maybe a haircut if you haven't one recently in a month or two. I geerally say go with some parfume but my hesitation is 99% of guys will overdo this. Parfums are strong. A small drop or half spray rubbed between the back of the wrist and then rubbed on the neck slightly behind the ears shoild be plenty. MOST IMPORTANT. Shoes. You dont need nice shoes. Just not dirty or old and tattered. Old, dirty, tattered shoes are a big no, no.


Venue selection
- pick a nice place with a memorable environment. Nice view, walkway, or nice part of town where there is vibrant energy. Nothing overly expensive or fancy though. This is a good way to set the tone early by showing you put effort into planning date details. Its always good if you haave an option to "extend" the date by taking a walk along storefronts, boardwalk, atrium etc. This is a good option to have if things are going well. Should be well public and well lit. Have some awareness for personal safety and comfort.

Conversation
- Lead the conversation BUT listen more than you talk. That means you pepper the conversation with opportunities for her to speak if she is shy. Not a big problem if she is not. But listen tonwhat they say and repeat or comment on what they say at critical points
-nothing negative, complaitts or venting. This is a fund date not a visit to your therapist or vent session with yoir buddies
- set the tone with some gratuitous but authentic compliments. About the venue, abott the venue staff, or anyone in your stories below.
- complimenting yoir date is tricky. I'd say if things are going well and you can pull it off withoit it being awkward, go for it. But if it feels forced, I woildn't do it. Keep it very light if you do go there "you look great, thats a beautiful watch/braceletee/acvessory. I'd stay away from wardrobe, hair, eyes, smile etc unless you feel confident.
- dont talk about the ex. AT ALL. Its in the past. Leave it there. They will ask and its a trick question to see how much you talk about your ex. Have an answered prepared for this question if they ask aboit divorce, ex. Something like it was a few years back, we decided it was best path forward etc. Minimal answer no need to go into details
- have some ice breakers ready (I was a little nervous but was looking forward to this, how was your drive, its been ages since Ive neen to this part of towm, ive been meaning to come here, its been so cold/raining/windy thes past few days etc)
- have some topics ready. Since it sounds like you helped her out with something thats an obvious one. But have other non controversial things to talk about. Do you like the food/dessert/wine/coffee? Maybe local, national, global current events that you are aware of. Keep it light and positive. And if possible relevant to your date. Did you hear about the new shop/restaurant opening in town, the local sports team etc
- No religion, politics, controversial topics
- Have a story or two about your kids, work, past, something you did recently (trip, home project, charity event)
- probably most important, have a story or two about something you are passionate about. Thats yoir chamce to shine. But don't oberdo it unless you want to bore them to death

The "Close"
The close is important if you want to have a subsequent date.
-keep an eye on the clock. Dont let the date drag on longer than it needs to. If possible, ask if she has a time limit and maybe set one for your self. Some may not like this but I think its necessary to keep things from dragging on unnecessarily.
- let her know IF you enjoyed yourself
- look for other cues or openings to plan a subsequent date
- Time your opportunity to ask for the next date if things went well. Read the room here. Was she bored. Looking at her phone/watch.
- "can we do this again sometime?"
- don't leave the date without knowing if you are doing it again. The planning can come later, but you need to know intent.

Other
Pay attention to body language for non verbal cues
- eye contact
- leaning in or out
- does she touch you with her hands or tries to get close
- is she distracted, looks bored?
- is she staring at her phone? This one is a deal breaker for me.
- is she smiling laughing when you say something mildly funny
- facial expressioms. Warm or cold


Good luck buddy! I hope you give us your post date debrief

Dating again after leaving an SM is very strange feeling, for sure! For me, I wanted to meet someone, but I was in no hurry to get into another relationship, so that took off some of the pressure and anxiety. Granted, first dates can cause nervousness and I did have that, but I tried to keep it light and just getting to know someone while also looking for red flags (ugh). I had a few not so great meetups, but the person I am with now we clicked on that first meeting, even with the nervousness of a first date. I hope all goes well for you and you have a wonderful time!

Wishing you the best dinnaken and hoping that whatever happens, you'll view it as a learning experience. I'm curious about why despite being divorced for 2 years, you're spending so much time alone and haven't ventured into the dating pool. There are so many interesting things to do -- volunteering, classes, sports, etc. that you can do to meet people -- not just potential partners, potential friends with things in common with you.

Almost 10 years ago, I went on my first date in 36 years with anyone beside my ex. I viewed it as a practice date as I was asked out by an acquaintance who was in a theater troupe I'd joined (got into theater in my 50s as I was crossing things off my bucket list).I didn't know him well, and, frankly, had never paid much attention to him though I did think he had a beautiful dog. His dating invitation came out of the blue. I used to post on FB invitations to any friends who'd want to join me for lunch. Usually an eclectic group of people would show up. He came one time, and casually asked me if I liked to see plays. He also mentioned that he liked to sit front row in plays. I mentioned that was what I liked to do to, so he said he had front row tickets to a local play and asked if I'd like to join him. A couple of days later, he asked if I'd like to have sushi before going to the play.

Anyway, I used the dinner to find out about him, and found out we had a lot of things in common: We'd both been on the board of our local political party, we both are atheists, we support the same causes, and his life reflected the kind of things i admire such as his serving as student body president in his community college while living at home with his beloved mom who was dying of cancer.

Anyway, I haven't been out on a date with anyone since because the guy I thought was a practice date ended up being the love of my life. Incidentally, he and I took things slowly. I was in rehearsal for a play so until that was over, we only had about one date a month for the next 2 months. We didn't have sex until 3 months after our first date.

Your mileage may vary. But whatever happens, learn from it and keep putting yourself out there. And congratulate yourself for being brave enough to go out with her.

Thanks for the update.
She clearly enjoys being with you.

Try another date and feel each other out for what you are looking for.