Wing Woman Fail…

I had said in my last blog that I would really take time to focus on dating. I would wear makeup, do my hair and put in the effort necessary to give my love life the best chance of success. I had no idea what that would mean…

Friday night I went to my usual karaoke spot! It’s a gay bar in a city about 45 minutes south of me. I had gone there for the first time on a date a long time ago. I love it there because I can credit it as the place where I got my karaoke confidence. The environment is friendly, the crowd supportive and some of my favorite friends are regulars. It’s a normal cheers bar with a rainbow twist.

It’s always funny because when I go there I dress to the nines. I have worn heels there (think baby giraffe) and then subsequently fell on my ass singing Partition wearing those heels. I was so embarrassed until the the whole place laughed and started clapping when I got up. It’s just one of my favorite places.

On Friday night, I wore a cheetah print v-neck sweater worn backwards with a black lace tank top, and jeans with UGG boots. I even had make up on with bright red lipstick. I was feeling… it!


So I walked in, paid my cover in quarters, and instantly ran into one of my friends. He gave me a big hug and complimented my lipstick! I love a good lipstick compliment and seeing him 😉

I laughed it off and said something like “yes I love that I always get dressed up for here where there is zero chance of me meeting a straight guy”

He said “Well Jill you never know!”

I ran up to the DJ area to put my karaoke songs in and came back to get a drink. After a few sips of my Corona, my friend tells me about the new hot guy sitting at the bar. He was sitting by himself drinking a Miller Lite. My buddy is beyond hot and has his shit together so getting them together was going to be easy peasy.

I started to visually stalk the new guy and wait for my chance to pounce. After a while, and one song in, I see my other friend chatting with him. This was an easy in! I walked rover and started chatting with the two of them. I introduced myself, my friend talking to him and my buddy over by where I was sitting before (the matchmaker target). The hottie introduced himself as Sean.

I liked this guy immediately. He was friendly, laughed when my friend pulled him in close to smell his new cologne and smiled a lot. He had a great smile! He was going to be perfect for my buddy!

At one point my sweater came up and I said “yeah at a gay bar I wear my sweater like this” and turned around showing the deep V in the back. It was a stylish look — not a sexy look.

“Then at the straight bar I wear it like this” and pulled down the front of my shirt to a VERY deep V showing my black lace V neck tank top neckline underneath.

I would love to say that was a first for me at that bar… but I’d be lying. My boobs are a very popular topic with my guy friends that typically don’t deal with them.


Anyway, we all laughed and I invited Sean over to sit with my buddies and I. I was really killing this wing woman job!

There was one point when I was standing in between Sean and my buddy by a pool table. I was bragging about my buddy and some of his life/personality highlights (I didn’t have all night to provide all his highlights). Then I did a move where I moved out from between them so they could better see each other. I noticed that while Sean was being friendly to my friend his eyes kept going to me.

When Sean walked away to grab his phone, my friend whispered “I don’t think he’s interested” and I replied “I think he may be straight.” It was something that honestly never crossed my mind and I never assume at this place or try not to anywhere in life.

So after my friend leaves, I talk and talk to Sean. His smile continued to get bigger and bigger and my hopes were higher and higher that I was going to do the thing that is the worse action for any wing woman —  take the guy for yourself.

We talked about our jobs, our shared love for 30 for 30 documentaries. my dating podcast/blog and our dating histories— he had dated a woman for several years. It was at this moment that I fully realized he was confirmed straight! (he later confirmed he is indeed straight)

He told me he was traveling for work and had been to the bar once before several years ago. He liked the bar because it was chill and the people were nice. The last time he went there were 5 people. The chill atmosphere was not the case on karaoke night but he stayed because he was only going to be there for a drink or two.

Right before the bar closed I got up and sang my favorite go to karaoke song “Free Fallin” by Tom Petty. When I got back to my seat Sean looked at me and said “Tom Petty is my all time favorite singer. That was really good.” I smiled really hard outside and inside.

This is a video of me singing the song with a random guy on the App Smule…. You can hear I’m a little nervous and it’s not always in key… UGH.  Plus I hated having to do the video part. You can see I’m awkward af.

Click on the link below 🙂 You can listen to it while reading the rest of the blog… plus you don’t have to see my face.

We stayed until after the bar closed at 2am.  I couldn’t get enough of  Sean and while I stuck my foot in my mouth multiple times… he stayed. At multiple points in the night my friends gave Sean a really hard time…. he stayed. When I warned him that my buddies say I’m a bear without a net… he stayed. He kept staying… and smiling.

As we walked out of the bar there was a guy yelling very loudly and acting agressive. He was clearly drunk and yelling loudly at everyone. It was a scene and threw me off my game. Sean and I get to the end of the parking lot, gave a quick hug and walk towards our cars…. in opposite directions.

I was so confused… I thought he liked me. But I have learned I don’t always have the best radar for this….  I kept walking to my car with my head a little lower.

It was then that I heard the drunk guy begin to scream at a woman outside the bar. I turned around. This wasn’t something that I could walk away from and not get involved. So I started walking back. It was then that I see Sean’s car pull into the parking lot. He had seen me walking back and got out and stood next to me while I talked to the guy in a quiet voice. It worked to get him to leave, even though he called me names I hadn’t been called in a long time.

I was fine and I knew I was safe. The drunk guy was small, I kick ass, and Sean was there.

It was at this moment that Sean offered to walk me to my car. It was so sweet! I of course said yes. I really liked this guy so the extra couple of minutes was wanted. At the car we talked for a while longer, hugged and he turned away.

“Aren’t you going to ask for my number?”  I yelled at his back.

He quickly turned around and with that million dollar smile said “Yes! I don’t know why I didn’t”

He texted me before I even got home. It was a very sweet message where he said he was glad to get to chat, hear me sing and even used the word “Stunning” to describe me.  I called my sister on the way home (yes at 2:30 am) excited about the guy I just met. Then his message made me have those butterflies in your stomach that jump to your chest.

Since then, we have been texting a lot each day. We have a date planned for this Friday and I seriously cannot wait. I’m trying to keep my cool but it was has been a VERY long time since I have been this excited about a guy. Plus there have been zero red flags and we’ve had some pretty big conversations.

The good news is I think he’s excited about me too 😉   I’ll keep you all updated as things continue! Fingers crossed ♥

Actual text from him in the style of the 30 for 30 documentaries that we both love:










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