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Dating Update (Sorry it's so late!)

With finals last week and the rest of life getting crazy, and then my mother visiting last weekend, I've been too lazy to write an update on my most recent escapades, but here it is! Sorry for the delay. Without further ado, the very long and excruciatingly detailed update on my dating life...



First I'll do some updates on Awesome Date Dude ("ADD"), and then I'll write about Wednesday Night Dude ("WND").

Saturday Night with ADD (5/10/14)

I was unsure what to expect with this date — a casual text after a week of silence, with an invitation to watch the Miami Heat game with ADD and his friends at ADD's place. I debated outfits and makeup for a while, and settled on a natural look with skinny jeans, boots, a tank top, and a zip-up hoodie. And my sexy black lingerie, because you know... not sure if I wanted to have sex on the second date, but why not? Unfortunately, I had already done awesome cat-eye makeup when I realized it might come on a little strong for watching basketball...

When I got there, he buzzed me in and... the apartment was empty. Apparently his friends all already had plans for a Saturday night. I probably would have been fine dressing up a little more, haha! We chilled out, watched the game, listened to music, sipped drinks, smoked hookah a bit... But he didn't make a move. Or put his arm around me. Or anything really? I just rolled with it, whatever.

After a while, one of his friends came by, so we all hung out together and drank more. ADD changes the music to more of a Latin sound, something suited to moving more than chilling. We keep drinking, and eventually ADD invites me to dance. I'm drunk, but hey, that means I'm not self-conscious about my terrible dancing. He can dance very well, and I'm just grateful that I took some swing lessons a few years ago, and it's so. much. fun. Not sure what his buddy thought, but ADD swings me around the room and we dance for a while. It was incredibly fun, I had an amazing time.


Eventually, ADD and his buddy decide we're going to go to a bar nearby. ADD's buddy leaves the apartment for a few minutes to "take a call". ADD and I are alone. We make out for about five minutes and it is awesome. Then we all walk to the bar. He and I hold hands the whole time, we are all very drunk, he buys me a drink. The bar is a local hot spot, it's huge and packed full of people. His buddy goes off looking for women, and ADD and I dance and make out the whole time.

Eventually we go back to his place, and I stay the night. You guys can guess what happened ;) The next morning was also very nice, I didn't feel rushed, and we just chilled out and had more sex until it was time for me to get going. The sex was just ok, but we were drunk that night, and he was very hung-over the next morning, so I'll withhold judgement until a later date.


I was pretty drunk, so my insecurities came out a bit. At the bar, he was whispering how beautiful and sexy he finds me in my ear all night (and he has a fantastic accent). I'm more Christina Hendricks than Keira Knightley, though, and I know he went to school in Miami, land of bikini bodies, so... yeah. I mentioned this, but he just shushed me. I also definitely asked if he'd still call me if I had sex with him that night. He looked pretty shocked when I asked, but I don't really remember more. I think he must have answered nicely, or I wouldn't have slept with him. I don't think he remembers any of it, though, because the next morning we were talking and he said he didn't really remember anything after we got to the bar. Upside: I don't look insecure.

I texted to invite him over for a bonfire I was thinking of having on Thursday night, but I knew that he probably wouldn't be able to go, since he was going to be flying out for a family weekend early Friday. I was right, but I got a nice response. I have not heard anything since, but lack of communication seems to be his modus operandi. I had fun, though, so I would probably go out with him again.


Wednesday Night, with the appropriately-named WND

WND and I hooked up last Wednesday (5/7/14) because I had an itch to scratch and I hadn't heard from ADD in a week, so I was just moving on. Instead of just meeting for drinks and sex, we ended up talking literally the whole night, until around 5am, and deciding to have a date the next Wednesday, too. (He lives in Chicago and comes up for work every Wednesday/Thursday). He friended me on Facebook the next day, we text (mostly conversational, a little sexy) and Snapchat (nothing dirty) every day. I like him a lot. Like, a lot. Everything he says hits happy buttons in my brain, and they're not buttons that are easy to press.


So I was very very very much anticipating our date this past Wednesday. I was also very very very much hoping that my period would not come on Wednesday. I have a very very very regular cycle, and guess what... it was due on Wednesday. And it came. Five minutes before I left to meet him. Sigh.

He was supposed to have the whole day off on Wednesday, so we were going to meet at 2pm. Instead, his boss called him in to train someone in Milwaukee, so he would get into town at 5 instead.Not a big deal, plus it alleviated some of my fears about such a long date when we're just getting to know each other. WND told me to figure out what restaurant I wanted to visit, because he was going to take me out to dinner. (A real dinner date! I don't know how long it's been since a guy took me out to dinner...)


Because I know the area, I offered to drive us around/to dinner. Rush hour traffic was in full swing, so we decided to wait a little while before getting dinner. I went to his hotel and we just hung out — talked, listened to music, then made out for a long time. It was so good, but also very frustrating, because he's not comfortable with period sex. Bummer. Still, he's funny and we banter and he teases me in the nicest ways (sexually and mentally).

We go to dinner at one of my favorite places, a restaurant on a hippie-ish street in an old house with amazing Asian fusion cuisine and ramen. He loves the food, we sit and talk and never run out of things to talk about. He makes me laugh. I make him laugh. We talk about a lot of deep things. I lost my dad last year, at 21. (I'm just short of 23.) He lost his dad at the same age (he's just short of 29.) He gets it. So few people in our age range just get it. He doesn't pity me, he just listens and talks about his experiences at appropriate times. And then we joke more and laugh more and there's no pity or awkwardness. Nothing about him drives me nuts, and usually this kind of thing presents on the second date for me.


Eventually we decide to leave. We pass by one of the lakes on our way back to the hotel, so we stop and go out and sit on the grass to watch the water, talk, stargaze. It's beautiful. I could have sat there forever. It gets chilly though, so we head back to the hotel and just chill together more, then make out more and mess around a bit. We talk a lot. We cuddle. We fall asleep.

The next morning we cuddled for a while, then he suggests we get breakfast. I take him to a bakery/coffee shop near his work with the most amazing food. I offered to pay for breakfast, but he insisted that he would pay, since I'm paying my own way through law school and he has a real job. We talk even more, I hum a few lines of a song from an indie band I like, and he knows the song off the top of his head. We both saw them in concert last month, in different cities.


When he leaves, he gives me a long, slow kiss, right in the street. We still talk/text/snapchat every day. He was at the beach on Saturday, and sent me a video of himself playing guitar on the beach (he's actually really good — he just set the camera on the ground and played for a bit). When I asked what his apartment looked like (since he's seen mine), he did a shapchat video to give me the tour. He said that I should come visit for a weekend. We've already talked about him maybe visiting me for a weekend, because there's things to do/see that we can't fit in during a Wednesday visit. This is moving so fast, but I'm not seeing any red flags. I like him so much. Guys, I think I'm crazy about this guy. And it's still so early that it scares me.

Semi-relevant facts I cannot find a place to fit elsewhere: He likes Madison. He actually would like to move here (and told me this before we even met up to have sex). He is potentially looking for a new job. We have similar attitudes toward sex and dating, which is interesting. He is just as likely to initiate communication as I am.


And here's the complication: I'm working in another city for June and July, starting next week Tuesday. I'll be commuting back to Madison for the weekends, so I can have a social life, but I won't be here on Wednesdays. This coming Wednesday is the last time I'll be able to see him, unless we start arranging things and actually going out of our way to see each other.

It seems too early to talk to him about more serious dating stuff (this coming Wednesday will be our third date, I guess), but I don't want to give this up, so I guess we'll have to talk about it when I see him next. I really want to keep seeing him. I'm pretty nervous about this talk, but since he's mentioned weekend trips twice, maybe this would work.


This concludes the very long and detailed update on LemonadeLover's dating life. I hope it was mildly amusing in some way.

ETA: I have just begun developing a cold sore. Goddamn it. I'm putting Abreva and a cold sore protector on it, and maybe the universe loves me enough that it will be gone by Wednesday. I know this is a futile hope, but goddamn it, I don't need another complication.

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