Saturday’s Rate-A-Date: Ryan in Open Diary 2001-2018 (Pre-Prosebox)

Name: Ryan

Age: 30

Relationship Status: Never married, but seems very ready.

Occupation: Works with children at mental health center/city councilman

Length of date: 7 hours

We met: Well, he picked me up at my place. Unlike most of my dates lately, I trusted him right off the bat. Hm.

I wore: White hot jeans, a little black halteresque top with strappy dangle thingies on them (very technical there), super high stiletto slides, chandelier earrings

He wore: Jeans and a really great, striped dress shirt

We did: Dinner at a swank, brand new Italian place. They still need to work out a few of their kinks, but I had a nice time. I drank a little wine while he had Coke (he does not drink). Then we went to a block party where my friend Steffi was a hostess. I’d told her that I would try to stop by at some point on Saturday night and had forgotten about it when Ryan asked me out. Ryan was super sweet about it and drove us out there. I knew it had the possibility of being an ugly scene, and I knew that we would both be at least a little uncomfortable. But it was worse than I’d even imagined. I was trying to find an excuse for us to leave when he came up with a perfect one: underage kids drinking in Steffi’s garage. We were off and running. We then went to a quiet little piano bar type place where we finally got to settle down again. We even danced a little with the old folks and that was kind of romantic. But I could tell that Ryan was itching to smoke a cigar because the place used to be a cigar lounge…not any more. I asked him if he wanted to go to a cigar bar and he said yes. We left. We found a little couch in the bar where he smoked a decent-smelling cigar (I hate stuffy cigar smoke). We laughed because there was a wedding party at the bar. And not just the wedding party…the bride and groom were there too. People, this place is a dive. I love it, but it is definitely a seedy, smelly, dank, dingy, dive. We could hardly believe that the bride and groom would actually want to go there instead of the honeymoon suite or whatever. So we had a few laughs about that. Until a bunch of people came running up to me and practically fell all over me. It turned out to be Renee’s sister’s wedding party!! And one of the people falling on me was Renee! Yikes. Shortly thereafter, I felt like I needed to go home. Ryan was awesome and romantic and gave me just the right amount of attention and affection and knows exactly what to say, etc…but I really needed to go home.

Convo: Nice. Really. Um…I was afraid to broach too many subjects with him on the first date, as I can tell he has a past that he doesn’t want to dredge up now that he’s pretty heavy into the politic thing. I know he’s had drug and alcohol issues, but not sure exactly to what extent. So…I avoided some things purposely. Still, he was terribly charming (just like a politician, eh?) and extremely quick witted. I was left very curious, but definitely flattered.

Part of personality I liked: That sweet charm mixed with a healthy dose of chivalry that doesn’t go over the top and doesn’t seem fake or forced at all.

Part of personality I disliked: The possibility of deep, dark secrets and the fact that he can cover them up with sugar and honey so well. I’m pretty sure that there’s a temper in there too.

Part of appearance I liked: Boyishly cute

Part of appearance I disliked: So boyishly cute that he looks like he’s about 21.

Highest Point: His unusual complement about my shoulders.

Lowest Point: Feeling weird about Steffi’s party.

How it ended: He drove me back to my place and we had a small make-out session in his car. It was borderline steamy. I enjoyed myself.

Chances I’ll see him again: I saw him again last night. And he’s chomping at the bit to get together again sometime this week. What a change. What a pleasant surprise. Not sure if I like him.