Gray Dating after Divorcing a Cheater — Am I Back in High School?

After 42 years married to a serial cheater (someone with Chronic Cheating Syndrome or CCS) I filed for divorce. And now what? I am back in the dating pool. How does that work? I met my ex when I was 17 and had not dated a lot before that so I had little experience. And now all these years later here I am again. And the more things change, the more they stay the same.

I had a plan to find a great man to “show” my ex that I could find someone better than him. Maybe then he would be sorry for what he had done to make me finally leave him. I wanted him to have huge regrets.

Welcome to Dating Apps

What to do? All my friends recommended trying the dating sites. You can stipulate what you want and see if you “match” with anyone out there. And hey, I looked pretty good for 64, right? Not a day over 50 by some estimates. My cheater always insisted that I look perfect, and I had tried to comply. And I have my revenge boob job so what do I have to lose?

I am a researcher by trade, so I looked at all the apps out there. Most come with a monthly fee. The free ones are populated with creeps (including my ex) so I chose carefully. Match, Zoosk, and OurTime (for old people). I carefully curated my profile. Most of my friends put up old photoshopped pictures, lie about their ages, and write long profiles chronicling how sensual they are and what a great match they’d make. Not me. I put up real, unretouched pictures, told the truth about my age, and wrote one paragraph about myself. My thought process was that most men are going to look at the pictures, try to figure out what town you’re in, and maybe read a sentence or two.

It is a standing joke that all the old men in Florida where I live put pictures of themselves holding up dead fish and riding either a motorcycle or a boat. And they lie about their ages and how tall they are. I need a tall guy since I’m tall and I like to wear heels. Ex was 6'4" and very athletic looking. So all the fish guys were not a great start IMHO. I set up my profiles and oh, my. A deluge of guys responded. I showed my sisters-in-law and they were horrified about what I had to choose from. They had a field day swiping most of them away.

But there was one that got my attention. He was a retired airline pilot just like my ex. Wouldn’t that be a great revenge! So I agreed to meet the pilot. We went to an outside venue halfway between our two towns and had a drink. He wasn’t as tall as he had said he was in his profile but he wasn’t shorter than me. We met again at the most expensive restaurant in my town. He set it up and paid for everything. Great!

I went to his house. Lovely, well decorated, on a lake. And immaculate. He was very fussy about it too. If I used the sink, he ran over with a towel and dried it. He had also had a prostatectomy so sex wouldn’t work. No worries, I wasn’t interested anyway. He also liked porn. A lot. Hmm, red flag number one. I had lost a lot of weight on the “devastation diet” that comes along with the stress and heartbreak of divorce. And being older it had not been kind to my skin. He asked me if I had an eating disorder, then asked if the reason I wore shrugs, he called them “little sweaters,” all the time was because of the sagging skin on my arms. That was it. I left immediately. He texted me once saying he hoped I found what I was looking for.

Revenge plot didn’t work.

The second dating app guy had a sad story about his wife of 40 years just walking away from him, so he moved to Florida to live with his brother. We went to a nice restaurant and he was happy that I looked like my pictures. The second date was for a dance lesson and dinner. The lesson was fun, dinner not so much. He had a lot of conspiracy theories that he began to tell me about. I paid for the dinner and left. I think I understand why his wife walked away.

The third and last dating app guy was smaller and skinnier than me. And, he was married. Just looking around. Next!

Meeting Men the “Normal” Way

I gave up on dating apps. It was just too gross for me. I felt like I had put myself up for sale, like a commodity on the shelf. And the buyers weren’t what I had hoped for.

I had to take my car to a transmission shop for a mysterious (to me) problem. I went after I had been to the gym — so I was wearing gym clothes, sweaty, no makeup. The manager was a cute, tall guy who looked a bit younger than me, and we chatted and laughed a lot. I also chatted with the kid who was working on my car. He had a cast on one arm that he had gotten after he broke down the door on his cheating ex-girlfriend’s house. I can certainly understand that. We bonded.

The next day, the transmission shop manager sent me a text. “I don’t usually do this, but I would love to take you out.” I have heard that line a LOT since becoming single. I even saw my ex use it when I was doing recon and looking at his chats with other women. I talked to my friends and they said go for it. Our first date was at a beautiful oceanfront restaurant in town. He wore a suit and tie. And sent me flowers and a bottle of the type of wine I drank the next day.

Wait! How did he get my address? Oh, he had ALL the info from my car. And I lived in a gated community, so I wasn’t terribly worried. He was a very gifty. He sent a Michael Kors watch, a designer bag, lots of wine and flowers. My son was over one day when some flowers arrived and he just rolled his eyes. He really was not keen on my dating anyone. And I don’t like being fawned over. I know some women do but I don’t. Maybe I was too conditioned by the ex, I don’t know. When transmission guy showed me a “granny porn” movie with a woman who looked like me (older, short blonde hair, mole on her shoulder) I was done with him.

My friends and I all love to go to a place in our town that is a restaurant/dancing venue. All outside with bands that play music for older people (Motown, ‘60’s and ‘70’s soft rock). We love to dance and have a whole crew that goes, and we dance a lot. “My Girl” came on and none of my “friend boys” would dance with me. I saw a cute, tall guy swaying to the music and went over and asked him to dance. And he agreed! We hit it off and chatted a bit. We had a good friend in common. We did not exchange numbers or anything, but our friend called me the next day and said dancing guy would like to take me out, could he give him my number? He highly recommended him. He was a bit younger than me, had a great job, his ex was a cheater, and he had screwed up kids too. Perfect match! I said yes.

Dancing guy took me to the same restaurant that transmission guy had. And he also wore a suit and tie. Wow. We did hit it off and dated for almost a year. Everyone liked him. My son did for a while, until he felt like it was getting too serious. I took him to meet my family and my brothers and sisters-in-law liked him too. But they all said he was too nice and not for me. He is a people pleaser just like me. He was talking about marriage. I was still healing. He still has problems from what happened to him in his marriage to a serial cheater and so do I. And again, I cannot stand being fawned over. Oh, and of course there was porn. I eventually broke it off, but we have remained friends.

My last date happened many months later. I was out with friends at another outdoor restaurant/dance venue. Lots of old people there. The JLo song “Let’s Get Loud” came on. I know a dance routine to that so I did it alone (a couple of glasses of wine might have helped). It got a lot of attention. One guy in particular, a retired cardiologist, was so impressed that he invited my friends and me to his house. A $2,000,000 house (yes, we looked it up). He asked me out and took me to the same lovely oceanside restaurant as transmission guy and dancing guy had. He did not wear a suit and tie though. Then we went to my favorite dance venue and danced until they closed.

I had met him in a grocery store parking lot and when he took me back to my car, instead of letting me get out he grabbed me and tried to stick his hand up my skirt. I wiggled away. So then he tried to put his hand down my shirt. I jumped out and left. He called for several days leaving messages that he was in love with me. I ghosted him. WEIRD!

Next

So, what is next for me? I don’t like dating apps, the “normal” way of finding men hasn’t worked too well, and here I am alone. It feels exactly like I am back in high school from the drama and gossip of female friends to the plethora of men that are just not right for me. I am kind of tired of the whole scene.

I think my healing is not over. I work all day alone in my house, go to the gym, then try to find somewhere to go to be with people because I am lonely. I drive 12 hours to my hometown every few weeks to visit my family and make sure my mom is being cared for. I have tried dating and it just isn’t working. I really don’t know where else to turn at this point.

I could write a book about all the men that have contacted me since learning that I divorced my ex. Everyone from his friends to childhood friends of all my brothers who have learned that I am single (I’m sure the brothers would just LOVE that) to friends from high school. It is weird and kind of scary. Then there is the pornography problem. They all seem to have it. And it messes them up, I think. My divorce attorney said something memorable when my divorce was final: “Don’t get involved with anybody else. At this age they’re all crazy.” He may be right!

I am 66 years old. I think about what is left of my life and I think I do not want to spend it alone.

I am trying to figure out what I like to do. And I don’t have a clue. When I was married, we did what the ex wanted to do. I never developed any hobbies. I guess the next step is finding me. My problem is figuring out how to do that.