I owe you all an upDATE from the other night.

First of all, it’s so funny how different the men all are that I’m going out with in terms of relationship readiness. They are keeping me on my toes!

Fresh off the heels of The Doc assuring me he’s NOT interested in anything serious, I meet up with this other guy – an ex, actually.

Well, not technically an “ex” as in boyfriend, but a man I’d casually dated several years ago during my phase where I was not relationship ready.

We always had a good time. He’s funny, charming and a total gentleman. The guy once delivered flowers to me after a simple misunderstanding just to make sure we were cool.

He’s financially stable, divorced for a long time and has two grown kids out of the house. He just turned 48 but looks and acts much younger.

During the time we were “dating,” this guy fell for me hard. Like, head over heels. I had some sort of a clue back then, but really didn’t know the extent of it…

One night last week, I was surfing around on Plenty of Fish and there he was! We had originally met on POF, and it was cool to see him single and available.

We exchanged messages and he said he was JUST wondering about me! How strange.

I was uber curious to see this guy again. I had changed. I was ready. Had he changed? Was he still ready? Was the timing better now?

It turned out that his birthday landed on the day after we selected to go out. Cool! One stone, two birds. We’d celebrate.

It took awhile to figure out where we’d meet for dinner. I suggested a few places and he was pretty indifferent.

Now, normally that’s not a big deal, but this is the guy who when we were first dating used to pick two restaurants before our date, and DRIVE to them each, check out the vibe and ambience, look at the menu, and actually talk to the manager to get their feedback before choosing which venue would be best.  Screw Yelp. Just ask this guy…

But, whatever, I just took it as maybe he was feeling guarded and didn’t want to extend his gentlemanly-self quite so soon. After all, I kinda rejected him and broke things off last time.

So we arrive at Bottega Louie, a nicer Italian spot downtown LA. I love this place. He had never been.

We have the “Wow, I haven’t seen you in a long time…” jitters and strangely enough we launch into conversation about dating. Online dating, dating in LA, what he’s experienced since we had last been dating, what I’ve experienced, etc

(Btw, I’ve found this conversation to be a pretty typical one with guys nowadays. Nothing too extensive but we definitely chat about dating and meeting online without any stigma. In the past? Stigma.)

So he’s actually telling me that dating hasn’t been going so well for him. That it’s been hard because he started working the graveyard shift over a year ago for his job and that makes it impossible to date. He admits he’s a bit rusty.

He also tells me he no longer believes in the institution of marriage.

Screeeech! Hold up. Say what?!

This dude HAD changed. But why?

So he proceeds to tell me about a “relationship” he had after me that really messed him up. He says he got played pretty bad by a conniving woman who wanted him to chase her for a year when he really wasn’t interested, and when he did switch from only liking her as a friend to all of a sudden realizing he loved her, she broke it off because the chase was over. Messed up. And I felt bad.

That was over two years ago and he’s over that now. But it had changed him a bit.

So I’m listening to his stories. We order a fancy Italian pizza and drinks and continue to chat.

He’s still making me laugh, in between stories and I’m enjoying his company. He’s really one of the good guys and I can still see that. I tell him I’m having a good time and it’s good to see him and catch up.

And then he drops the bomb…

“It’s good to see you, too. But as far as I’m concerned, we should be sitting at this table as husband and wife.  You should have long since been my girl.”

Ummm…. excuse me??? Did you say WIFE?! #WhatTheWhat

He proceeds to tell me that he held back a lot when we were first dating because he knew I wasn’t really interested in anything long term. He is acting timid and kinda shy and totally vulnerable now, but he continues to share his feelings.

I was “the one.”

The whole time my mind is reeling. Is this guy serious? Is it worth checking out? Maybe we should date again…

He assures me I’d be the happiest woman on the earth, that we’d be great together, and that bit was always easy with us.  We clicked.

I tell him I’m confused because earlier he had said he didn’t believe a happy marriage was in the cards for him. He cleared up that I was a different situation. I was different from all the other women he’s dated over the years.

Oh.

I begin to understand. I’m acting super sweet, caring and aware of his vulnerable state, all the while. But still processing this news…

So the restaurant is closing down by this point and the lights start to come up as bus boys clear all the tables.

It’s getting late, it’s a “school night” and I have to work in the morning, so we head out.

I drive him to his car parked farther away, and he’s making me laugh so hard by random things he’s saying in our small talk conversation. (Sense of humor is MUST for me in a match.)

He reminds me that the “ball is in my court”, he gives me a quick kiss goodbye and we part ways.

So there ya have it! The proposal-ish conversation.

It’s been 5 days since that date and I’m still not quite sure what to do. He’s definitely a different person nowadays. I suppose I am, too. There are new things about him that I don’t love and that rub me the wrong way, but I dunno… Maybe I’m sabotaging what could be a really good thing? Heck, I did it once with him already! (even though the timing was off)

And I further suppose that starting over with each other might just be a good idea. I’ll continue to date and meet other people until I figure things out.

The shenanigans of a single woman in her 30s in Los Angeles continue!