The Midlife Debutante Dating Over 40 A Lesson in Organic Attraction and Chemistry

A Lesson in Organic Attraction and Chemistry


Dating First Kiss Midlife Debutante Blog

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Before I begin, I’d like to say that I discussed this post with the person I am writing about. You see, a long time ago I learned that I had the right to share details about my own emotions. My private thoughts, experiences, misconceptions, and perceptions as they happened. I am an open person, and veritably, an open book.

But when it comes to writing about other people, you should consider that they may not be as open. They may not want the minutia of their life or experience with you, to be shared. And so, I had a conversation with him, and he assured me he was okay with it. And that maybe, he may even like reading my thoughts on what transpired.

I had an unexpected and wonderful weekend. Something that reads like an after-school special, given the circumstances. But if I am to journal my life as a single person, I want to share the good things that happen. Not just stories about healing, or working through trauma and negative life experiences.

Because when I experience joy, it is worth noting. When something really good happens to me, it is worth celebrating. Moments of elation, life learning, and unexpected happy consequences of happenstance. I can usually predict bad things happening. Good things always take me by surprise. I’m never prepared for them.

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Getting to Know a Special Friend

Who knows why you are attracted to some people? After a negative and confusing experience, I had actually decided I wasn’t going to date for a while. The experience hurt me far more than it should have. I don’t connect easily with people. I have walls for a reason.

For several weeks I was talking to a man. It’s hard to explain, but the conversations flowed so naturally. I crave conversation and relation with other people. And so, I delighted in each one. Whether it was on the phone, or joking around in a social group on Facebook. Or by IM’s in Facebook Messenger.

I started to talk a little bit about this person. With people I trusted. But not from a romantic angle. I found he was well-traveled, and shared my inquisitive nature about the world. A humanist. A real grounded good soul with values I admired. Yes. We could (and should) be friends.

He was articulate and creative. Responsible and deep thinking. And when we got on the phone hours would pass. And there was always a hesitation to hang up the phone. Both of us enjoyed the conversations so much. The humor and sarcasm we shared were great. We liked many of the same things. And hated the same things too.

A kindred spirit! Whether male or female is always welcome in my world. I’m lonely. I miss my family and friends back home. And I am stretching to build myself more ‘family’ type friendships in Austin. To balance that wheel of my social needs.

We talked about girls he was interested in dating. I joked about a couple of guys that were pursuing me. And how they were failing to do much but increase my anxiety and despair. I liked him, in that I felt I could trust him. He had no clear motive, except to enjoy some good conversation. And a laugh here and there.

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Live Music and a Friend Date

The man I had gotten to know, and shared so much with, is also a musician nights and weekends. He is actually in several bands around the Austin area. He invited a bunch of people to a gig in downtown Austin. Two other people from our group coordinated with me, to go to the event. And his band would be playing. I was looking forward to seeing my new friend on stage.

He told me that he had invited a girl he may be interested in. They had talked briefly, and he thought she was pretty. I was excited for him. Hey, as a group of single friends, when one wins, you all win. Because those of us that haven’t connected with someone special, find hope in positive outcomes.

I had no doubt that they would connect. She was lovely. A firecracker and vivacious woman. Confident, and she seemed very fun. I liked her (what little I knew about her). I crossed my fingers for my friend. I knew that he was amazing. I thought she was pretty and cool.

Along the way spending time chatting, more than a couple of friends asked me if there was something more. Did I like my friend in a different way? After all, I am capable of having platonic male friendships, right? I prognosticated on that point in the blog. “No no no… we’re just friends. And I think he is awesome!”. I wasn’t lying. I hadn’t met him in person, but from what he had shared, I was cheering for him. Seeing him find someone that could delight him and make his life fun? That would be a victory I’d enjoy seeing.

I thought the world of him. And I wanted him to be happy. He deserved that (and so much more).

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Dressing Sassy and Swinging My Mojo Bat

You never know when you are going to meet someone awesome. Every morning, I do my hair and put on my makeup. What if my dream guy is at the dog park this morning? These are the things I think about when I make myself make the effort. I am alone, but life is mysterious. If you are open to good things, they can happen at any time.

We got to the bar, myself and another male acquaintance. He too was hunting for a companion. I encouraged him. Ever the cheerleader for the happiness of others, right? I needed to feel sexy. I needed to feel pretty. And I guess, I wanted to maybe catch the eye of 1 or 2 guys at the bar. Nothing would happen, but at least I would feel it was a step in the right direction. If I got noticed, even a little.

Thigh-high boots, oh my! Except with my short legs, they went all the way up. That was okay though. I paired it with a black skirt, shirt, and jacket. No thighs showing! I was covered up but sassy. I did my makeup rocker chick style, with dark eyes. Kind of gothic I guess, but apropos to the venue. Straightened my hair, and wore my expensive perfume. The kind that makes men smell my hair discreetly in the HEB grocery store.

I put a simple request out to the Universe. “Please don’t let me be the one standing alone, while everyone else connects passionately around me. Even if it’s just a flirtatious conversation. let me have a brief moment of male and female connection. I need that. Badly.

I felt pretty. And confident. And looked forward to the evening with friends. #HappyVibes! And if all went well, my red-headed friend would meet a man. My male friend would make a connection with the girl he invited. The other male acquaintance would find a young woman to marry and make babies with. And I, maybe, would get flirted with.

Meeting for the First Time and my Ungraceful Attempt to Have a Poker Face

Once inside the bar, I texted the musician “Dude, where you at?” He generously agreed to introduce me to some of his friends that would be there. So that I wouldn’t be standing alone, or feel awkward. I thought that was nice. Really nice and considerate of him. I have social anxiety and it gets worse in crowds. So bad, I can have a full-blown panic attack. I’m getting better at hiding those.

Suddenly, I heard a “Hello Skylar” from behind me. Get ready for the cinematic (but honest) description. I turned around slowly, and there he was. My friend. The musician. Tall, dressed in dark clothes, and my face flushed immediately. “Oh my God he is good looking!” was the inner narrative… followed by some panic. “Oh crap! Ohhhh crap! Noooo… you aren’t allowed to be… attracted to him. You are becoming friends! Stop that… stop … his shoulders, holy crap. Look at his hair… oooh his eyes… God damn it Skylar! Lock that crap down! He is a FRIEND. Not food! Stop looking at him like he is a cheeseburger!”

I didn’t know what to do. I had to stop the chatter in my head. We have an ongoing joke that I only side-hug. Never full-frontal hugs. Because to me, those are special hugs. Like, “hey Daddy I like you” kind of hugs. It is part of my single girl meets boy repertoire. And I reserve it for special occasions. Like, never deploy it. It’s the only move I have.

Suddenly, I was full-frontal hugging him. Laughing. Joking at the same time. My funny girl comes out in moments of intense awkwardness when I need to deflect emotions that bother me. Like, imagining kissing him. STOP THAT! Or putting my arms around those shoulders QUIT IT SKYLAR! Ohhhh big hands…. that smile… that smile… UGH!

He chuckled and gave me a big squeezing hug. And my knees started shaking. OMFG! PULL YOURSELF TOGETHER! How many bars have you been to? This is your FRIEND. Straighten up right now and regain your composure! Except that my face was red. My cheeks were burning. And he smelled better than cookies.

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Hands Off Someone Else’s Date (Girl Code)

With the elation and waves of attraction I was feeling, the sobering thought came tumbling out. He is not my date. He is not here to see me. He has a hot chick incoming. She is much better looking than me, and I think, far more engaging, confident, and interesting. Yep, they are going to hit it off. I know it.

And with that, I felt a shift in me. A “fish are friends, not food” moment like in Finding Nemo. Someone with a stronger claim on this amazing man was incoming. And I am not his type. I am absolutely not his type. I mean, who likes a chubby marketing nerd with post-divorce emotional shrapnel? I wanted to leave, but couldn’t. I wanted to go home and distance myself from what I expected would happen.

Because this attraction flew under the radar. I (on my soul to God) didn’t know it was there. But I felt a tsunami reaction to his physical presence that frankly, blew me over. So, since I was in this impossible scenario of wanting to be a good person, fair to his lady date, and fair and loyal to my friend achieving his goal for the evening, I made a decision.

They were going to kiss. I was going to be heartbroken. So, I had better get drunk to make sure I could cope with it, with poise and grace. And that is exactly what I did. By the time I reached that determination and flawless strategy, my red-headed friend had arrived. Back up! Awesome. Now I could wander off and let whatever was going to happen to my dreamy friend, just happen. Like it was supposed to.

Hands off. He was not mine to pursue. Nor was he interested in me that way. I mean, compared to the blonde woman, I was peanuts. I put on my best silly fun girl mask. Headed to the bar, and proceeded to drink shots. Because, for someone who doesn’t drink like, ever, that was the best idea ever.

Feeling Connected By the Music and Moved by a Performance

He took the stage with his band. “Don’t stare at him! Seriously Skylar.” But my heart was pounding in my chest with full force. I love guitars (always have) and have dated a couple of musicians in my hey-day. I should also explain that I am an audiophile. I have sensitive ears that hear layers of sounds. Part of ADHD maybe, that hypervigilance. But when it comes to music, I hear and feel the entire tapestry of every note and every instrument. And love it.

Since I couldn’t stare at him (didn’t want him to think I was a drooling idiot just because he was on stage) I decided to focus on his hands. They moved up and down the neck of the guitar with such grace. The complexity of what he played and every note came floating at me. No, he would not see me staring at him. But I was entranced by his talent. Have references! I dig a guy that can play guitar. Also, violins and pianos do it for me too.

Compared to some of the other bands, he was a shining star. Complexity isn’t the word. His skill and talent were like a beacon. And the notes from his guitar felt like they were floating into my body. I moved to his music gently and closed my eyes a few times to experience it. Might have also been partially due to being completely and utterly drunk at this point. I was ready for someone more qualified than me, to be in those long, strong STOP IT!!!!!!! arms.

And I would be happy for him. I really would. I mean, I think I would? YES I WOULD! Because I care about this person and he deserves that. He really does. STOP BEING SELFISH! Do you really think someone amazing like him would EVER be interested in anything more than friendship with you? Stick to your lane Skylar… predominantly psycho’s. That is what I seem to attract in great numbers. To the extent that I truly had stopped many weeks ago… after two more bad dates finished off the last of my optimism for 2021.

Dating in Austin Over 40
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The Bombshell Arrives and I Quietly Dispaired

My brain and anxiety was off the hook. I couldn’t compete with her. I am not remotely in her league. And clearly, if blonde bombshell is his type, I am not REMOTELY HIS TYPE. How could I be? I am just a chubby brunette Canadian that talks way too much. Nothing to see here. No threat to the gorgeous blonde either. And, I also liked her a little too and wanted to get to know her.

The blonde and I had had an awkward impromptu conversation. She had asked me if there was anything between the musician and I. Of course, at that time, I had not met him. I felt the possibility of a deep friendship, and was very happy to have his company. But the whole giddy-up feeling? That wasn’t there. Until of course, that night when I met him for the first time face-to-face.

Could he tell I was attracted? OH CRAP I HOPE NOT! What kind of friend would I be? Ridiculous… this situation was utterly ridiculous. Tipsy and feeling a strange combination of being swept off my feet by his proximity, and being a disloyal jerk by disclaiming any interest in him to the bombshell, I was miserable. You couldn’t tell. I was telling jokes, having fun, going out onto the patio. I retreated with my red-headed friend and promptly decided to flirt with another man. Because that would set my barometer straight, right? I know, I am a horrible human being sometimes.

But there was the bombshell. She looked radiant. My shoulders dropped. PATIO! STAT! And when I got to the patio, another man started flirting with me. He had a red shirt on and said he was in one of the bands. #OhHai! Zero attraction by the way. My head was playing scenarios about the guy I wanted to be with. Who was about to go sailing off to the sunset with a lovely lady. Who was not, clearly, me.

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Dancing and Playing It Cool: And Avoiding All Eye Contact

I like to think I have a poker face. I do not. So, aware of this precarious situation, I tried to stay away. On the patio, the smart butt musician from another band flirted relentlessly. He said “You confident girls are all the same. You talk $hit but you don’t have the guts to make a move or reciprocate. You are all too insecure to….”

Then I kissed him. I put my fingers around his shirt and pulled him in for a meaningless smooch. No tongue. No passion. Zero sparks. But if you wave a red flag like that in front of a bull, guess what happens? It seemed the fastest way to put him in his lane, and stop him from talking continuously. It worked!

Me: “Now go back to your friends and tell them you scored a kiss from a drunk Canadian girl. Call it a victory and walk away”. Several times through the rest of the evening, the redshirt dude kept checking in. “No sir, I am not your takeout. You bore me. You irritate me. I get that you want to bless me with your body, but honest, thanks. No. No. Never. Shoo!”

I bravely took a couple of tokes off my Delta-10 vape (legal in Texas) bucked up and went back inside. Ready to see them kissing. Knowing how I was going to feel. Conflicted. Upset. Happy for my friend. Jealous. My head was spinning. That could have also been the tequila, however. And the shots hadn’t worked. I saw him standing about three feet behind her on the dancefloor talking… and he looked over toward me. I immediately gave him a face like “WHUT?” in a comical way and quickly looked away.

Yeah. They were going to hit it off. Damn it.

And a quiet voice inside me was whispering: “But we like him… a lot. We can’t just do nothing!” And then the adult voice stepped in and said “Not only will you do nothing, but you will mind your manners. We’re talking about your integrity here. It’s not about YOU! It’s about him and his night. Get back in your lane Missy and act like a grown-up.

So we walked to the dancefloor and stood beside them. Her back was turned to him, watching the stage. Once, forgetting myself, I turned and he was behind us three girls. I looked up into his eyes and quickly corrected myself. Yeah, ignore him. Make yourself ignore him. Stop it. Stop thinking about … those eyes. Those soft gentle eyes… and those big shoulders and…. AAAARRRGHHH!!!!!!!!!!!!

An Unexpected Departure Early and Conversation

The blonde bombshell didn’t look like she was having a great time. Hard rock and mental isn’t everyone’s Jamba Juice. I love all music and found it invigorating. My lovely red-head and I danced playfully and hugged, the way girls do in a bar. I danced with the bombshell too. She seemed uncomfortable. I wanted her to have fun.

She hugged us and said she had to leave early, after checking her phone a few times. The night was still early enough I guess for her to do something else. We said goodbyes, and I looked at my warm-hearted and wonderful redhead. She was smiling like she read my mind. And the blonde leaned in and whispered: “You’d make the perfect rocker girlfriend”. I felt horrible.

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I still wasn’t going to do anything but hey, they didn’t kiss, right? PHEW!

Me: “Hey you, want to do a shot?” (Because more alcohol was exactly what I needed).

Him: “Yeah that sounds good. What do you like?”

Me: “You choose, I’ll have whatever you suggest.”

For the record, shooting Jameson whiskey is the WORST idea ever. I don’t drink hard liquor anymore. And it felt like I had swallowed battery acid. It burned. Like, all the way down. Of course, I made the faces of someone facing their death by shot… and I heard him chuckling beside me.

Him: “You are so adorable.”

My head: “Oh NO you don’t… you aren’t going to unbalance me again with your… profound hotness and … personality and stuff!”

Me: “Whatever. I could probably drink 5 more of those. Kidding. That was horrible! I never want that shot again…”

And then he moved closer. And moved closer. And suddenly, it was on like Donkey Kong! A kiss the likes of which I haven’t experienced in a long time. Because what was behind that kiss were hours of deep conversations. Sharing. Trust. And now this mysterious chemical crap that was happening to me. The kiss was hungry. But sweet. And for a moment, I forgot where I was. I felt like I was on the moon, kissing him back with all the things my brain wanted to say, but couldn’t.

Say something! SAY SOMETHING COOL! Damn it!

Me: “Woah”.

Him: “Yeah woah… that was um…”.

[Insert me blushing like an idiot again]

And then he smiled at me. And I got that feeling again. Okay, music man. That first one took me to Venus. But caught me off guard. I am NOT going to let you run this situation entirely. I am going to assert my confidence, and show you that I am not subject to the fleeting emotions of infatuation when we are just supposed to be friends…

[Insert me pulling him by the shirt the wall behind us and… commence more passionate kissing].

I LIKE YOU I LIKE YOU I LIKE YOU I LIKE YOU… And the room spun. Could have also been the tequila, like I said, but the word I used later when I drunk texted him was “immolation”. From my nose to my toes.

Great. Just great. You know that makes me a hypocrite about what I wrote about platonic friendships, right? Jesus Christ Skylar…

But I didn’t want it to end. I really didn’t.

And neither did he.

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