I met up with Scott....

After talking to Scott for weeks and weeks, he moved to Chicago during a weekend that I could get there...... I was waffling between caring whether or not we met...there have been a few flags, and I don't think he will be husband #2, but I sort of left the ball in his court.

Initially, weeks and weeks ago, we had said we were going to do drinks, but as the date approached, he said that drinks were too intimate. He suggested lunch or coffee.....and I ended up suggesting a Saturday afternoon walk, since he decided to keep the Sabbath and I wasn't going to be in town on Sunday.

We met....and walked....and talked without a pause for 45 minutes..which is all the time we had, because I had something else planned.


I wasn't sure that I'd like him in person. He's smaller than husband #1 was. But I might like him a little bit. I won't be able to see him for a few weeks yet.....so we'll see if he wants to see me.

First date with Adam

Met up with Adam for sushi in the Chicago suburbs. First impression.....not altogether unattractive, kinda nerdy, but sweet.

We talked for a solid hour, and it was nice. He was accessible in spite of his chemistry genius. He was a decent story teller. I'm not sure I laughed hard, but I smiled.

At the end of the date, I felt like I should hug him, but I didn't really want to. Not that hugging is a big deal, but throughout the date/meal, there was just not a part of me that wanted to see him naked. Or get naked with him. Or felt confident that he would know what to do with my naked body.

And he's moving in September, and I won't even be back in Illinois for a few weeks yet....so what's the point really? I guess if we met and I wanted to climb on top of him, then I would have tried to set something up, so that I could climb on top of him in a few weeks, but I don't.

He sent me a text two days after our date "Good morning! Hope today is better than yesterday. Any chance you'd be interested in a second date?"

So sweet. It really did melt my heart a little bit, and I hope I let him down gently while still keeping the door open for a friendship once I move down there. I said that I didn't think he is quite what I'm looking for. That I want to find a partner who is ready to start a family in the next year or so (or within a year of starting a romantic partnership). He admitted he's not in that position..

Of course, this all is such a load of shit. That I'm going to have to go through for who knows how long. But hopefully not for too long.

The end of Aaron.... and maybe a pause from men for a bit

I thought things with Aaron were going fine.

We talked for weeks, we had what seemed like a great first date. And great physical chemistry.

And we made plans for date number 2.

And then he calls me and says "I don't think it's an emotional fit. I don't think you should come and see me this weekend. I'm walking away"

Very little explanation. He admits I'm very sexy, but doesn't think we're as compatible as apparently I thought we were...

And that despite him saying that he wants to keep it casual, he said that he's actually not cut out for casual.

So.......yeah. This person, who lost his brother last year, apparently doesn't have the emotional sensitivity to keep seeing me.

Actually, I think he's seeing someone else that he started seeing before me, but he wouldn't admit to that, which I find annoying.

Every rejection, or every hurdle is going to re-open the wound of missing husband #1. Of not believing that I have to go through this shit, after already having gone through this shit and finding the most amazing man for me, ever.

That this Aaron guy didn't even compare to.

<<sigh>>

I guess there are other things I need to be focusing on anyway, but it was a pleasant enough distraction for the time being.

...

Not everyone is okay with dating a widow...

I messaged a guy, he seemed interested in grabbing a drink, until I told him my story.

To which he responded with this:

"My sincere condolences.

I hate sounding insensitive, but that revelation changes my outlook. I don't think I am the person you need, and I know you are not the person I am looking for. Hope everything works out for you.

Best,

Erick"

No doubt, I'm not for everyone, but it still stings a little. I'm trying to cast a wide net, because at the core of myself, I don't want to be alone.

I wish I could have husband#1 back. I know he didn't mean to leave me. But he did. I want someone else to understand my jokes. To think I'm cute. To want to procreate with me.

It's okay that it's not Erick.

Talking to Scott again...

So it's been weeks since Scott and I started talking, and things got heated, and then simmered down. And now we're just 2 weeks away from actually going out.

We recently FaceTimed, and I still think he's cute. And his phone battery died just as I unzipped my dress......but he got it charged up enough, and I might have showed him my boobs.

And I don't know if I regret that. There are already some flags as to why I think he might not be husband #2, but I do sort of want to climb on top of him, and I want to know if it'll be as good as it is in my head/in my dreams.

I feel like at almost 4 months into this widowhood, I might be about ready to have sex. With someone who is gentle with my heart. And maybe a little rough with some other parts.

Scott isn't sure I'm emotionally ready for what he's looking for, but I told him I don't think I'll know until I'm in it. And that I know what it is to sustain an exciting relationship...so there's that.

I asked him not to write me off yet. But through texts, he made some comment about that I was being nasty to him.

I didn't like that, because I don't think I was being. He's kind of emotional, and I think in the end, I need someone a little more mellow. Just like husband #1 was.

Date #1 with Aaron....

So, Aaron and I talked for a few weeks, and because his family was in town the weekend that I was going to be in Chicago, he suggested that we meet not until 10pm, for drinks.

Though it's normally later than I start my night, it was sweet that he wanted to meet me, even though he obviously had other family obligations.

From his pictures, he seemed cute. From FaceTime and his texts, he seemed sweet. Like a nice guy. A few years younger, and 10 inches taller.

At 7:30, he texts and asks if we can move the date to 9, because dinner ended earlier than he expected. Score! I was anxious to meet him, and now we had more time together, since we both said that we would probably be ready to wrap things up around midnight.

We hug. He tells me I look great. We order drinks, he pays. We talk. And laugh. And talk. And move to a quieter area. And talk. And drink.

And the whole time, I'm thinking "I really hope he kisses me. He's cute."

It's 2 hours of talking, and he mentioned that he generally doesn't kiss on the first date. He reads the situation, but it's not a given. So I go downstairs to the bathroom, and from there, text "I know you don't always kiss on the first date, but if you kissed me, that'd be pretty sweet" ..... I wasn't sure if it sent though, because I was downstairs.

So I get back to the table, and he goes "I think we need to pump the brakes on this. I think we can be support for each other, but I'm not sure we want the same things, so it might not be wise to go down a romantic path"

Or something to that effect.
I stared. Shut down. Rubbed my hands on my face.

Pump the brakes? PUMP THE BRAKES? ON WHAT? DRINKS? All we were doing was talking and drinking....... I texted him....but all I asked was for a kiss. What the HELL?!?

So I tell him that I'm not really sure what I'm looking for, but I'm pretty sure that the first few guys I date after husband #1 will not be husband #2, and that I'm casting a wide net and keeping it casual.

He said that maybe he misunderstood. I said all I was hoping was that he kissed me tonight. He apologized. I said "then fucking come here and kiss me."

He obliged. And it was nice.

And we went back to my friend's place (she was not that happy, but is a good friend, and hopefully a little gift will be adequate damage control), and all of a sudden, we were naked in bed together. I told him I wouldn't sleep with him, and I didn't.

He told me my "tits are spectacular" and as we laid in bed, naked bodies next to each other, legs intertwined, he tells me that I'm amazing.

I say thanks, but .....MIXED MESSAGES MUCH? I wish I had asked him what prompted him to say that, but now I fear it's too late.

He said he had a great time, and to be honest, so did I....minus that one awkward blip/misunderstanding. I told him I was nervous about being naked with another man, who wasn't husband #1, but .....it surprised me with Aaron. It felt comfortable. Nice. .... and kinda hot.

But we're keeping things casual and might not be in the same city again for a month or so..... hope to have an update then...

A new man, let's call him Aaron

After things have kind of cooled off with Ryan, I started talking to a new guy, who we'll call Aaron.

Aaron and I talked online for a bit, then through texts, and when he didn't respond to one of my texts for hours, he called me.

We chatted for 20 minutes, and it was in this conversation that I told him of my widowness. And that I found a story about how he lost his brother less than a year ago.

So we have this instant connection. And I'm waiting to see if we have more of a connection than that, but so far it's sweet.

And we have a date in Chicago in a little bit, and I'm hoping it goes well. He is a little younger, but already seems more mature than both Scott and Ryan.

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.

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*"

.....
.....

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.