Date #2 with Ryan

I'm pretty sure that date #2 with Ryan will be the last date with Ryan. He is a nice guy. Understanding. Smart. Not altogether unattractive, but I'm pretty confident that he's not the new guy for me.

We made plans for me to go to his apartment to watch Curb Your Enthusiasm, and for him to make me dinner. We talked all week about the tentative menu, and he seemed really excited to cook for me. Let's be honest, a meal where I can watch TV, that costs me nothing, I was looking forward to it too.

So I get to his apartment in Lincoln Square, that he shares with two other 20something year old boys. He opens the door, and I am smacked in the face with the smell of boy.

And not like boy's cologne, but full on boy living, breathing, sweating in the apartment boy.

Strike 1. But I can look past it. I can. They are nose blind to it, and soon I will be too.

We sit on the old, grimy couches, in front of the coffee table that is a slab of glass on top of two plastic hampers. One is pink and one is blue. The table is littered with papers, remotes, cups, paper towels......  He mentions that he has nice stuff. That none of this stuff is his. His stuff is in storage, and costs $100 a month to store. He's doing that instead of having his stuff in this apartment. Okay, so strike 2, but I can look past it. He wants me to believe that he's adult enough......and I almost do.

I came over for dinner, and after watching TV for half an hour or so, I said I was getting hungry. He asked if I wanted to help chop up stuff for the fondue that he was going to make. I didn't really want to.....but of course said I would help. I'm a good chopper, but it was our second date....he should still be trying to impress me...and maybe he was, but it just sort of felt like he didn't quite have his shit together. Like he isn't a good enough planner.

So we ate the apples, carrots, bread and broccoli in the fondue, and the next course he had planned was steak, but at this point it was 9pm, and the steak was still wrapped in plastic. I didn't really feel like waiting half an hour and eating such a heavy thing, so I asked him if he would be offended if I didn't eat steak. He kind of seemed like he would be, but I told him it would be a waste, that sometimes I don't like to eat large amounts all at once...

We keep watching TV for a bit; HBOGo keeps on stalling. His arm is around me, I'm kind of nuzzled into him. It's not terrible, really. Except for that my neck starts to hurt after a little bit. But I find myself getting bored, and while he is nice and all, I found myself really wondering about my physical attraction to him.

So I ask him, point blank, if he wants to fool around for a little bit.

We go into his bedroom....bed unmade, and I gesture for him to take off his shirt. And he does. And it's really hairy. Front and back. Something I'm not used to at all. I used to tell husband #1 that he had the perfect amount of hair...everywhere really. Ryan and I are kissing, his shirt is off, and he unzips my dress, so I'm standing there in my bra and panties, and I dunno....it's fine and all, but not great....

We climb into bed - me, with the knowledge that there's no way I'll be sleeping with him, but also with a curiosity as to what I'm working with.... I find my way to his zipper, after swatting his hand away from my panties... and telling him that whatever he was doing to my nipple wasn't really doing anything for me.

I unzip his pants and find my way in.......to disappointment. I'm sure it's average. But I was used to above average. And I loved every minute of it. I offered to play with it for a bit, without actually seeing it, but he said he's never gotten off with manual stimulation from a girl.

This is where I know something's up. "Are you on antidepressants?" I ask. Sure enough, he is. And blood pressure medication. There's no way I want to fight against the meds. There's also no real chance that I want to watch him jerk off while he looks at me. And yes, he did ask if I'd be okay with that. And then asks if it was weird. I said, "yes, that's weird." In 9 years with husband #1 I don't think he ever jerked off in front of me. And that was okay by me.

So I tell Ryan that I'm not even going to try if it's not going to happen, and then went to put my bra back on. I just felt like everything was too dirty that I didn't really want his hands wandering in my nether regions, and there wasn't much else to do.

I told him shortly after that I wanted to leave. And I left, after a few more kisses. And I got in the car and drove to my friend's house....and I cried for husband #1 most of the way there.

Going out with Ryan...thinking about Scott

It still feels a little weird to be thinking about/talking to two different men, neither of whom are husband#1....but my friends are encouraging me to cast a wide net. To play the field. To have a little fun.

Even though I had the most fun with husband #1, I think they're right. I shouldn't get too into any one man at this point. It's unlikely that the first or second guy I date or hook up with will become husband #2. Not impossible, but unlikely.

So I'm seeing Ryan, who is really nice. Who texts with me all the time. Who told me he likes me......but I can't help but think about how sexy Scott was in the video I saw of him lecturing...to an empty room.

Scott and I decided to put in pin in whatever we were developing since we aren't going to be in the same place for several weeks yet. I kind of get it.....it is really just a fantasy right now, even if we did FaceTime....but in the meantime, it's nice to have Ryan as a distraction.

And I may have bought a sexy new bra and panties to have in my back pocket...just in case.....

My first first date in 9 years

Ryan and I exchanged long messages on OkeeDokee online dating site, and soon those long messages turned into long emails, and dozens of texts throughout the work day.

He is also a lawyer, but already lives in Chicago, and after having enough to talk about with each other for weeks, I asked if he wanted to grab drinks.

He also asked at some point how I ended up in the city I currently live, and what was bringing me to Chicago. I told him it was wrapped up in a sad story, but that I would share it with him if he wanted. Through mutual friends, he was able to figure it out, and apologized...both for finding out, and for the fact that this was my story...and he also said this was new for him. But he decided to keep talking to me. Score 2 for men in their 20s/30s not being scared off by the baggage that automatically comes with a 20something year old widow.

So Ryan and I talk a lot about the possibility of making out. He assures me that his experience with the French horn makes him a very good kisser. I tell him husband #1 played an instrument too. Maybe I shouldn't have. And maybe I also shouldn't have said that I miss having sex with husband #1. But I did.

Ryan and I decide to meet for drinks at a place near Lincoln Square, but I decide to bring two girlfriends. I tell him beforehand, so he doesn't feel ambushed, but I also tell him that it's what I need. That this is my first first "date" in 9 years, and I don't know what to do. How to be. What to say....

So my girlfriends come, and it's the three girls and Ryan. And he talks to them almost more than he talks to me. He tells us a story about some unfortunate boss he had. And after they text me that they think he's nice, and after drink number 2.5 for me, they excuse themselves to go on a quest for pizza. Or chocolate. I don't really remember. I don't really care.

So here we are, Ryan and I sitting at a table. His sweat from riding his bike to the bar has dried. He's not exactly my type physically, but I'm getting more drunk by the minute, and he keeps touching my arm. My hand. My shoulder. It's obvious this "making out" that we've been talking about might happen soon.

I take another sip. "I don't know what I'm doing. My life is so complicated"
He moves his chair closer, and grazes my hand.
"It's not so complicated. It's okay"
He leans in.

We kiss for a minute.

.....

<<WHAT AM I DOING. KISSING A MAN OTHER THAN HUSBAND #1. WHAT AM I DOING KISSING A MAN AT A TABLE IN A BAR??!!>>

.....
I finish my second gin & tonic and order another.
He told me about a time he ingested pot on a trip to India, and I asked him to tell me his story, and then I shared with him the time that I made pot brownies in college. (I did it wrong. Got super high. Threw up. A lot.)
......

We kiss some more.
.....
It's midnight and the stupid Chicago ordinance that outdoor 'beer garden' spaces close goes into effect. We have to go back downstairs. We finish our drinks. We get ready to go on a quest for pizza. <<Need food to avoid hangover tomorrow>>

On our way out, we wander back upstairs, which is closed to the public, and yet there are people up there. The door is closed, so there's this sort of secluded alcove at the top of the stairwell. We make out some more......and then I tell him that I want to show him my boobs.

I don't know why.
I don't know why I want to show him. Or why I chose to do this. I was pretty drunk, but Ryan had mentioned that he is a boob man. And I thought he'd appreciate my 36Ds, and I wanted to have them appreciated. It'd been months since they'd been appreciated in person.

"Wow. those are pretty fantastic."

"Thanks, Ryan. I think so too. Do what you will with them."
So we're making out in this not really private alcove at the top of the stairwell in this bar, when he moves his mouth to my breasts and puts a nipple in his mouth. And nibbles just a little bit.

We make out a little more. I put the boobs away. And we go look for pizza.
...
It's Chicago, so we find pizza in approximately 3 minutes. He buys (which he totally doesn't have to, but I appreciate it).

We finish our pizza, and he shows me where the single person bathroom is on the side of the restaurant that's closed. I bring him in the bathroom with me. And we make out some more. And my dress somehow comes down, again. And his mouth finds both of my nipples this time.
"a little more gentle" I suggest.

My hand was able to tell that he was enjoying himself very much. I bent over as I let him have his way with my ta-tas.

We kiss some more. I apologize for maybe giving him blue balls, but I also don't really care. I don't think I'm being a tease, or am leading him on, that's just all I was ready for. And he seems like a nice enough guy that he understands.

He held my hand while I waited for my Uber.

<<My first first date in 9 years. Overall, a success, I'd say...">>

My foray into the (online) dating world.

About a month after husband #1 died, I put up pictures on two online dating sites. We'll call them OkeeDokee and HeyDate. I only put up pictures, no words, because I didn't know what words to put.

Do I put "widowed" or "single" as my status? Do I open with "I haven't done this in a long time, but I promise I'm pretty normal" .... or tell these strangers a little bit about my story...or just let them reach out and hope they appreciate me for my humor, wit, curiosity....and then once they decide they like me enough, drop this bomb on them?

I didn't know the answers so I just put a few pictures up. And browsed both sites to see what was out there.

At first, no pictures or profiles excited me at all. In fact, they sort of depressed me. I was married to an extremely bright, funny, motivated, manly doctor, and these men paled in comparison.

And then some time passed, and I became more bold.

And someone sent me a "flirt" on HeyDate. And he seemed cute enough. Very different looking than husband #1. Scott looked different in every one of his pictures, but in most of them he had facial hair, which husband #1 never had.

Scott had a slightly receding hairline, while husband #1 did not.

Still, Scott and I had some similarities, a few mutual friends, and he seemed cute enough. We exchanged messages on HeyDate for a week, when he gives me his number, to take it offline, as they say.

<<Is this a thing? Do people just give their numbers to strangers? Apparently>>

So after spending a day of looking at apartments in Chicago (the city I decided to move to, after being left alone in a city where I had no family), I texted him, deflated, that I hadn't really found anything that I thought would work for me.

And thus begun an 8 hour texting session, intertwined with at least three drinks, as I hit the town in Chicago. He tells me his dad is a doctor, with the same first initial of his last name as mine (and my late husband's). He tells me the second letter of his last name, and it's also the same. Now I'm getting nervous. I tell him I don't want to tell him my last name. He says this is questionable, but I tell him it's because I don't want him to Google me.

Not helping my case here, I know. I explain that when he googles me, husband #1's obituary comes up, and I thought that after knowing that, he might not want to talk to me anymore.

Turns out I was wrong. Weeks later, he is still talking to me. We talk about what's going on with work, and both of our impending moves to Chicago, and what types of places we might want to go to.

In one of our texts, he says "Quite frankly I know in my head it's silly to be getting involved with someone in your position, but I am excited by you. You are sexy, dynamic, strong, intelligent and quite interesting....I want to be with someone who excites me"

Scott started to excite me too. Even as he talked about writing his boring law articles and reading his boring research, I found myself hanging onto the elusive ellipses that indicated a new thought was coming.

Scott gave me the courage to add words to my profiles. So I wouldn't put "widowed" - it's a lot to handle, and might pull me out of searches because most men my age would only expect someone 50+ to have that box checked.

And I started browsing OkeeDokee and sent another lawyer a message about Curb Your Enthusiasm, since we're both fans.

And that's how Ryan and I started talking......