I had been on seekingarrangements.com (SA) for a couple days and I was itching to go on a first meeting. My roommate, Tiff, was flying to her home state that next morning, and I wanted to go on a date before she left, so I would have someone to call if anything went south. I had been chatting with this guy, lets call him OG (since he was my Orginal Gangsta POT lol). He had first messaged me on SA’s with this message:
How has your week been?
I enjoyed your profile. Would the occasional afternoon by the pool, steady financial help, some movie nights, daytime adventures, intimacy (if we decide to go there), Some trips to Colorado (if you like to travel), nice dinners and a discrete long-term friendship work for you? I take care of you and you take care of me.
Let me know if you’re interested…
I liked OG because he was polite, engaging, and honestly, straight to the point. He wasn’t super attractive in his photos, but he was in good shape and had a clean cut appearance. He wasn’t a big texter so if I didn’t reply for a few hours or even a day, he wouldn’t send me annoying “hello you still there?!” texts. He was the only POT that wanted to have a phone conversation before asking me to meet him. I told him when I was free to chat and I sat there staring at my phone, anxiously waiting for it to ring. I was so nervous I felt like I was going to throw up. But, when it did ring (right on time), and I said “hi” with my voice all shaky, he didn’t seem weird or scary. He honestly sounded like Matthew Mcconaughey…. He asked me how my day was, what were my plans that evening, and just simple small talk. It was easy to talk to him. The conversation was intelligent and engaging, and I found myself telling him all about my plans for grad school or potentially moving to Portland. We talked for about half an hour before he asked me, “So how did you end up on this site?” I wanted to be honest with him. I told him about my friend, how I was always physically and emotionally attracted to older men (no I don’t have daddy issues) and how I wasn’t broke but I did have debt etc. He was understanding and nice. I then asked him the same question.
OG’s story went like this: 8 years ago he got divorced. For four years, he remained single and focused on his work. His main residence and home is in Aspen Colorado, but he had purchased a home in Scottsdale Arizona so he has a place to escape and play golf during the winter. He was self employed in real estate, and doing extremely well for himself. He goes back and forth to his home in Aspen and his home in Scottsdale for both work and leisure. Anyway, four years ago, he met up with a golfing buddy for lunch in Scottsdale. His friend brought a young girl with them, she was about 21 (he was 47 at the time). Anyway, his friend had to take a business call during the lunch which ended up lasting over a half hour, and OG and the girl completely hit it off while his friend was gone. They had a lot in common etc. Anyway, a few weeks later, she found OG on Facebook and sent him a message about wanting to see him again. Apparently, her and OG’s friend never really continued dating and just didn’t click (no drama according to OG). So OG and the girl started going on dates and ended up having a completely normal relationship for the year (normal besides the age difference of course). It was NOT an arrangement. He obviously paid for dates and such, but he never gave her money or supported her financially. Fast forward to the summer, and OG was itching to go back home to Aspen and escape the heat but he didn’t want to leave his girlfriend behind. She couldn’t come with him because she was working as a waitress all summer to pay for school. So OG told her that if she spent the summer with him in Aspen, he would double whatever she estimated to make for the summer. So she obviously accepted and they had a wonderful summer in Colorado skiing, hiking, etc. When they both returned to AZ in the fall, OG continued to discreetly help her financially. He told me she was always a little embarrassed by it, so he would usually slip an envelope of a $1000 into her purse every week. Their relationship lasted 2 years until she moved away to New York for work. OG tried dating women his own age after that but he found that he enjoyed the energy and company of younger women. He discovered SA over the past year and made a profile. He had one arrangement for 6 months that had just ended mutually. He took a few months off from dating, and then reactivated his profile. He said he saw my profile and said he thought I sounded intelligent and down to earth.
Not creepy, huh? His story was so genuine to me. I really liked how he sorta stumbled into being a SD from a normal relationship rather than pursing it. Before our conversation ended, he told that if we agreed upon an arrangement he would start off with an allowance of $1000 a week (which would increase as our relationship grew). He also mentioned he wasn’t just an allowance guy. He said for example, “if your phone or laptop breaks, I’ll get you a new one. You mention how you always wanted to see such and such play, don’t be surprised to have front row tickets mailed to you the next day. He then quickly added, “however, don’t expect to see the 1000 bucks the first few days we meet, I’ve had too many girls take the money and I never see them again. I need to trust you and know that you’re genuine.” Rather than being turned off by this statement, I actually felt bad for him. He seemed like a really nice guy and I imagined him liking all these girls only to get ripped off after a couple dinner dates. We agreed to meet the next day at 4pm at a restaurant in Old Town for a couple drinks.
Before our date the next day, I made sure Tiff had my location, and I told her if I wasn’t home by 7pm, she needed to worry. I told her even if I texted her something like “I’m staying out late” not to believe me. Yes, this might be a bit paranoid, but it was my first time meeting someone online, and I wanted to be careful. I had been to the restaurant once before so I was comforted in knowing that is was an extremely popular place and we were meeting during the day. I thought I was nervous to talk to OG on the phone, but meeting him in person? I was shaking the whole drive there. I probably contemplated turning around 12 times. I got there early on purpose. I wanted to be in control of where we sat. I chose a table on the patio. I ordered a beer while I waited. Looking back, this is definitely not SB etiquette. I was probably a bit too casual with my denim shorts, tank top, and flip flops… and ordering a beer before he got there was probably a bit too bold. But I was so nervous inside and I wan’t to give the appearance of confidence. I heard a familiar “hello” from behind me. He caught be off guard by entering through the back entrance. I quickly stood up, smiled, and gave him an awkward hug right as he was going in for a proper handshake… I cringe thinking about it lol. Anyway, he sat down and called over the waitress. He ordered a beer too, a fancy one though, compared to mine. I told him I loved to drink beer. He glanced at me and said “that nice. As long as you work out regularly, it shouldn’t be a problem.” WHAT AN ASS HAT. WAS HE IMPLYING THAT I WAS FAT? OR THAT I CAN”T DRINK BEER UNLESS I WORK OUT? I didn’t say anything back. I thought the date would go down south from there but it honestly didn’t. Besides the rude(ish?) comment about me and beer, our conversation was as natural and engaging as our phone call. He made me laugh as he told me funny stories about being cat fished from SA. His first date ever he thought he was meeting a 22 year old blond girl only to be greeted by a 50 something overweight biker chick. He said he still had a couple drinks with her to be polite, but after that, he tried to be more careful. He asked if I would be interested in ever going to Aspen with him on the weekends once we got to know each other more. I told him yes, and I could see that this answer really pleased him. I mentioned I loved traveling and he said we could do trips to NYC, Chicago, and Hawaii if I wanted. Suddenly, the beer comment seemed insignificant. Maybe I just over reacted? He ordered another beer and asked if I’d like another. I said no, too embarrassed to get another one. I didn’t like how this 51 year old man was making me feel insecure about my looks, and I had some thoughts about the whole power structure that rests in a SD SB relationship. I already felt like I needed to please him and win his approval, and it was only our first date. He was so calm and confident. I felt insignificant compared to all his success in life. I reminded myself that I held a sort of power too. My youth was a novelty and he couldn’t attain this realtionship normally… if he was serious, he would be obliged to pay for my companionship. After an hour and a half, he got the check and we wrapped up our conversation. When he pulled out his wallet to get his card he also pulled out a $50 dollar bill and handed it to me. “Gas money for this date,” he said. He knew I only lived 10 minutes away. I awkwardly took it, fighting off the urge to say “no thanks” to the generous offer. He looked at me and said, “So what do you think? Would you like to see me again?” I was surprised by his boldness in asking me this right then and there, and honestly, I was happy that he liked me enough to ask me out again… I said yes and we agreed that he would reach out to me when he figured out his schedule a little better. He was flying to Cleveland the next day to spend the week with his 11 year old son from his previous marriage and then he would go to Aspen for a couple days. He said we could go on another date, dinner this time, maybe in a week and a half. I told him I looked forward to it, and this time we hugged goodbye without awkwardness.
When I got home Tiff was eagerly waiting to hear every detail. In a silly way, I pretended to be all posh and I whipped out the $50 dollar bill waving it in the air. “Let’s talk about it over dinner. My Sugar Daddy is buying.” We laughed and decided to eat at Buffalo Wild Wings. I told her every detail and she was shocked that he gave me money for just meeting him. I told her this wasn’t uncommon from what I read in my research and $50 bucks was actually below the norm for first dates. She asked if I would see him again, and I told her yes. During dinner, OG texted me to tell me he had a great time and looked forward to our next date. I immediately texted him back thanking him for the dinner and cash, and that I hope he has a safe trip to Cleveland.
Well that’s the story of my first date of many with POT’s. Success in my opinion. I didn’t get kidnapped, I got a free drink, and $50 bucks. Maybe the SB life wasn’t as dirty as I assumed. In my next posts, I describe other first dates, and the continuation of OG….