RAD: Jim, Poolside in Open Diary 2001-2018 (Pre-Prosebox)

  • Sept. 8, 2009, midnight
  • |
  • Public

I know you’re expecting an update on the Girls’ Trip, but I’m still processing it (as well as organizing the photos!), so I’m going to give you this little update instead (had set up this date before I left on the trip, and this is from yesterday afternoon):

Name: James

Age: 45

Relationship Status: Divorced, two adopted boys

Occupation: CEO of investment company

Length of Date: 3 hours

What We Did: Met for poolside cocktails at hip downtown hotel

He Wore: Poolside attire: shorts, tee, flip flops of some sort, sunglasses

I Wore: Sundress, sandals, sunscreen, sunglasses

First Impressions: He was walking across the street as I was valet parking my car, and I saw him and waved. He waited inside the lobby for me, and I noted that while he didn’t look exactly like the photos I saw, I think it was because he’d let his hair grow out a bit. And although he’s a fellow redhead (hee!), I don’t really like how he’s wearing it right now. Plus, extremely bushy eyebrows (whoa!!). Luckily, that’s nothing that can’t be changed. The rest? Has a REALLY nice body. And because he was wearing poolside garb, I’m going to have to hold comment on the way he dresses.

Convo: Very free-flowing. We both seemed to have so much to say, and one topic led right into another. He comes from a HUGE family in New England and has moved around quite a bit due to his work and his past marriage. He told me about his adopted boys and the visitation situation. Told me about his varied and pretty fantastic career (one of his partners has made some amazing business decisions that have left her a multi-multi millionaire, and I’m pretty sure this guy has done the same). We talked about travel and music and all the places we’d love to go, do, and see. We touched on our internet dating experience and our non-internet dating experience (he’s hidden his profile since we set up our date). He told me that he loved my feet, and at one point he actually rubbed my feet for a bit! That was a little odd for a first meeting, but I kinda liked it! He complemented me just enough without going overboard. I could tell he was really attracted, and I felt somewhat attracted and pleasantly surprised…especially since I was SOOOOO wiped out from my New Orleans girls’ trip. Ugggghhh!

High Point: No real defining high point moment. It was all good. I guess I was just pleased with the fact that he was really into me and completely has his shit together (at least by all appearances).

Low Point: And no real defining low point moment, either. I mean, the only thing I have issues with are superficial appearance stuff and that’s…well, whatever. I guess that says more about me than it does him, right?

How It Ended: After about 2 ½ hours, I noticed that he was looking at his watch every now and then, so I think he had other plans for the evening (we’d met at 4 for early cocktails). I had a leeeetle bit of hope that he might ask me to have dinner with him, but it was absolutely fine that we didn’t continue, because again, I was tiiiiired. So we peeled ourselves off of the poolside chaises and he walked me outside (we held hands while walking out). He asked me if I’d like to see him again, soon. I said yes and we made plans to meet at the restaurant next door to the hotel on Wednesday evening. And then he kissed me. And for some reason it took me off guard. I could tell he was a good kisser, but I didn’t want to make out in front of the hotel, so I kissed him just a little bit and then pulled back after kiss 4 or 5. Wow.

Chances I’ll See Him Again: I will on Wednesday unless something happens.

Lesson(s) Learned: It’s somewhat excruciating to have a first date the day after you get back from an insane girls’ trip, but not impossible!!


Last updated 5 days ago


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