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I just found that as women and men age, they get more tainted by their experiences. They create within themselves a negative bias as a standard operating procedure. I went on many dates with women in their 40s, and what I found consistent between all of them was they were immediately looking to find out how I was going to hurt them, even from date one.

The next woman was someone I would call a “girl next door.” She probably shouldn’t be on the website, and she wants an emotional connection, but she needs financial assistance. So I dated her for four to five months. After two months she said, I don’t want money anymore, I just really enjoy getting to know you. It really told me she wasn’t looking for a long-term monetary benefit, and that you can have a real chemistry-laden relationship with someone.

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t we are meant to be changed by our life experiences. We are not human time capsules or mosquitoes trapped in amber. But the issue isn’t whether or not we are shaped by our experiences; rather, it’s the pressure we feel to alchemize our traumas into trophies. So much of modern-day self-improvement has roots in toxic positivity and our need to feel that we are Doing It Right. The book asking readers if they want to come out of [insert trauma here] a better person. The Instagram influencer posting that pain can become growth, with the right mindset.

The third woman I call the “mercenary,” and she was the most dangerous person I think I ever met. She scared the shit out of me. She would say anything to make you think she loved you. She lied about not having a boyfriend, not living with him, got all the money, gifts, trips, and plane tickets, and when her boyfriend finally threw her out, she came crawling to me. So she ended up moving in with me for a while, and then I got set her up in an apartment. Once, I got really ill, and I told her what was going on, and I said, hey, look we need to have a real relationship, or this isn’t going to work. And to this day, I haven’t heard back.

I’m a founder and CEO of a global software company. My net worth is north of $50 million (£35 million). I travel a lot, but I’m based in New York. I was divorced about 3.5 years ago, and when it came time to get back into the game, I realised I couldn’t go back into conventional dating. I’m 50 years old but I probably look 38. I’m incredibly fit, I work out all the time, and I have the mentality of someone in their 20s because I just love to have fun. I jump out of planes, you know? I’m just one of those guys.

I spent $200,000 (£150,000) while dating on the site, and about 90 percent of that was on the third woman. I bought her a lot of jewellery. I’d buy her a ring, she would lose the ring or say it got stolen, and I’d buy her another ring to replace the ring. Then her rent, it was $3,500, $3,600 (£2,700-£2,800), plus a security deposit. I know. It was sort of like, hey dude, what are you doing?

My schedule just prohibited it. When I dated conventionally, it always followed the same pattern: Meet a girl, get to know them, they like the vibe. Then I start my crazy travel schedule and there’s an awful lot of stress and texting. When are you coming back? Where are you?

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Amy Cesal is a designer specializing in data visualization. She is a co-founder of the Data Visualization Society and currently serves on the board. Amy is passionate about building style guidelines for data visualization, trying to make everything, including charts, accessible, creating bespoke data visualization and experimenting with the boundaries between data and art. She holds a masters in Information Visualization from MICA.

Over the next two months, the age difference was slammed in our face. I remember I went out to brunch with her and her friends, and someone was whispering, you know, Whose dad is that? It didn’t really impact me, but I saw the look on her face. When we talked about it later, she said she wasn’t necessarily prepared for that. So we decided to remain friends.

There were three women I met on the site. The first woman was the “upfront woman.” I met her for a drink and she was very open about the fact that as long as there was some chemistry, she would meet with me and sleep with me for money. Unfortunately, that’s not really who I am. I need more of an emotional connection with someone, even though it might sound weird in that environment.

Then I happened to meet a friend’s sister for dinner, and the sister was 31 and we talked for 6 hours. It was so incredibly refreshing. It was just amazing to me. I thought, maybe I should start to pursue younger women. But then it became clear to me that conventional dating wasn’t going to work. I wasn’t meeting younger women in the bars I went to, and when you go on a site like Bumble, you’re aren’t going to find many women on there who are open to dating a 50-year-old guy. So I found Seeking Arrangement.

I didn’t expect monogamy but I was asked for it. So I told her, okay, well you have to be upfront with me, not just honest. If you have feelings for someone else then just let me know and we’ll cut it. That should be the best part about a site like Seeking Arrangement is you shouldn’t have to lie. Like, this is who I am, this is my situation, if you want to be with me under these conditions then we’ll be together.

Amy Cesal is a designer specializing in data visualization. She is a co-founder of the Data Visualization Society and currently serves on the board. Amy is passionate about building style guidelines for data visualization, trying to make everything, including charts, accessible, creating bespoke data visualization and experimenting with the boundaries between data and art. She holds a masters in Information Visualization from MICA.

But the thing was, I was exposing her to my entire world — I have kids who knew about her, my ex knew about her — and she wouldn’t expose me to anyone. She was saying all the right things but her actions weren’t matching what she was saying. So I told her, either you change or it’s not going to work. And then, ghost.