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.....

Real messages - Part 1

Because sometimes, you just can't make this stuff up, I decided to intersperse my posts with ACTUAL verbatim messages that I have received on dating sites. So far, I'm only on "OkeeDokee" and "HeyDate"....

I just don't think I can ever understand what goes through some of these people's heads.
There are a few different types of men out there, I'm learning. Slowly.

The over-sharer/one who tries to tell you everything he thinks you'll want to know in the hopes that you'll feel an instant connection/want to blow him:

"Got two older brothers, two step brothers and one baby sister. I like to go shopping, watch movies, go out to dinner, listen to music, watch NFL, watch NBA, love to cuddle, love to text, I'm respectful. I'm a nice and honest person. Love video games. Looking for a relationship. I live at my own house. I will never cheat on u. like movies and music. Love Sex. Want to text babe:)"

I want to add my own judgments and comments here, but I'll just leave it with this: So basically, he's telling me he's a person. Who exists. And doesn't adhere to traditional grammar rules. I know I don't always either, but it's usually for emphasis or to make a point. Also, this "man" is 24. Doesn't warrant a response.

Then there's the....let's call him bold/unconventional...and not really in a good way:

"Hey there! Let me start by saying I am aware of how forward and inappropriate this might be if you're not that open. I'm a (relatively) normal (slightly geeky) professional with the unfortunate juxtaposition of having absolutely no time for dating or getting to know people and an insatiably high sex drive. Since I also have a thing for hooking up with people I don't really know, and because you miss 100% of the shots you don't take, I saw your profile and wanted to see if you'd like to get together today or soon to let loose and have some fun without judgment or strings attached. If you're not, thank you for reading and have a nice day. If you're open minded and don't think it's too socially unacceptable I'd love to get together with you today. What do you think?"

"shot in the dark, have any interest in a submissive guy new in town?"

"hii, would you like to slice me up with a scalpel?"

And then there are the ones who try to start with flattery....not sure what to call this type yet:

"Woaaaaaaah, what a profile and what a figure. I totally don't expect a reply from you, because that can only happen in my dreams!"

"Okay, I'm hooked with the photos, I guess now I'd like to hear(see) her speak :-)" --- Okay I can admit this one isn't TERRIBLE, but he's 10 years my senior (dealbreaker) and not my physical type.

"So I don't want to come across as disrespectful, but honestly you're too beautiful for your own good lol. But straight up no bullshit, I'd love to get to know you sometime. Over coffee, drinks, a pool game or planting a tree I don't care I thought it'd be worth coming by to see if we could get to know each other so...here I am. But before I become your new best black friend, find out your favorite color, ice cream flavor, I wanted to know something. If a guy really wants to be in your life, what's something he should know about you before hand? Like you aren't some kind of crazy cat lady are you? Also where would you travel to if money wasn't an option? - This novel is brought to you by the Reading Rainbow. *que song*"

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Open to hearing your comments, if there are any readers out there.

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......

An introduction

One of the biggest voids I felt after my husband died was that I had no one to send flirty texts to. I am still in love with the man who we'll call husband #1. I always thought he would be my only husband. I told him often that he was my funniest friend, my best friend in the whole wide world. He tucked me into bed one night, and the next morning, I woke up, opened the bathroom door, and found him, lying there. Dead.

It shocked us all.

I will always love him, and yet, I find myself wanting to look for love, or at least flirtations in other avenues. If he was here, I wouldn't need to look. But I'm a (young) woman with needs. With no children. Who wants children one day.

We were going to start to try to have children the year he died.

So I'm on a quest to find husband #2, but acknowledge that:

1. I may have to kiss some frogs to find someone who still may be less of a prince than husband #1
2. The men I date/talk to/sext with are probably not going to be my next husband
3. There's no timeline for looking for or finding love in this world of widowhood
4. I'm a statistical anomaly. I'm younger than 30, was with the same man for nearly 9 years, and now I'm alone. When I never thought I would be. This might be too hard for some men to handle.

The two men that I'm currently talking to, both know I'm a widow, and both admitted that they'd never been in this situation before.

No shit, sherlock. Neither have I.

But knowing that there are at least 2 men out there who want to meet me anyway gives me hope. It's reassuring. And I'm thinking along the way, some interesting things might happen.

If you're not into the dirty details, you probably should stop reading. But I think if you keep reading, you'll have almost as good of a time as I'm trying to have, as I start Chapter 2.