Date #21: Tina the Loss
This was another surprise, in the best ways. Tina was a few years younger than me, with two teenage kids, and a profile that was "meh" at best. She looked pretty and wasn't fat, so I swiped on her. Most swipes go nowhere, hell, most matches go nowhere, so I sometimes loosened my standards to find a needle in the haystack.
This one turned out to be maybe my best match ever, though potentially dangerous and I fumbled it completely.
Tina was fun from the jump. She had a great sense of humor, roasted me perfectly, and dripped sarcasm all over the place. My schedule was busy with other dates so it took a while for me to get her out, but after a few weeks it was on. I still wasn't sure what I was walking into when I pulled into a spot at her favorite sushi place.
She pulled in moments later and when I greeted her at her truck, I was blown away. She was PERFECT. Absolutely beautiful, but not in the high maintenance way. She wore a little makeup and was dressed very casually, but my mind was on fire. She was on fire.
5'6", lean but not skinny, big tits (DD's if I had to guess), a narrow waist, a little bit of hips and a perky little booty. She had eyes that sparkled and a smile that just melted me, wispy sandy blond hair down just past her shoulders and a very sexy half sleeve tattoo running from her shoulder on one arm.
We picked up right where we left off from text and flirted throughout dinner and beers. You could show me 1,000 pictures of beautiful women and I might not rank her at the top, but in person, she just had it. She had me in the palm of her hands.
After dinner I drove us less than a mile down the road to a shitty bar I had found on Google Maps, but the second I walked in I hated it. We found a table and I immediately made the call to go somewhere else. She recommended her favorite dive bar that was across the street from the sushi place and we sipped beer I hate, while playing darts. We laughed over bad date stories and she seemed into me, but I wasn't totally confident. Honestly, I was so blown away by her right off the bat that my mind was clouded.
It wasn't just looks either. Everything that came out of her mouth was perfect. Clearly, it really wasn't, but I just felt a great vibe with her and she was too God damn fun. She was, 100%, girlfriend material.
By the end of it, my mind was so damn fuzzy that I wasn't even planning on trying to kiss her. Even after the bartender asked if we were married and we made a cute couple while she was in the bathroom, I was still unsure. I was scrambled. To my pleasant surprise, I went for the hug and she just kissed me! Nothing crazy and I didn't push it, but it was nice. Cute almost. I was smitten.
We continued chatting back and forth until I scheduled another date for us. This one was special. It was the holidays and she mentioned she hadn't gone to see Christmas lights in years. We had also discussed our mutual love for oysters, so I planned on hitting the best spot in town to eat, then Christmas lights, then find a fun spot to chill at.
Oysters went swimmingly and I ended up with the biggest oyster I've ever eaten. I don't post much on social media, but that one - meat the size of my palm - went straight to Instagram. After finishing off our pitcher of beer, we drove to the lights display. It was a drive through setup where you tune in to an FM station and put through a giant parking lot, filled with lights synchronized to the music. It was pretty cool, but went by VERY quickly, so I tried to find a place to go to next as we pulled out.
Not paying attention, I pulled right into a giant outlet mall just as all the stores were closing at peak shopping season. Traffic jam.
We sat in excruciating bumper to bumper for over an hour, trying to figure our way out of the parking lot. I was totally embarrassed, figuring I fucked up completely, and to top it off, couldn't find a fun spot nearby. I was so focused on the lights I got overly confident with my knowledge of the area and failed to properly plan. We ended up going back to her little dive bar, each drank one beer, and she was ready to go home. Another little kiss, but I felt she had faded.
The guy who's so meticulously planned dozens and dozens of dates at this point decided to wing it with, to this day, the ONE woman who made me think "serious relationship" more quickly than any other. Then again, that was the danger with her.
In just a few weeks of chatting and two dates, I had "love" written all over her. I'm smart enough not to get ahead of myself and am always on the lookout for dealbreakers to protect myself, but every layer of that onion I peeled back, she just got more and more attractive. I'm not sure that I've ever so comfortably vibed with another woman in my entire life. Why couldn't I have met her in my 20's?!
FUCK!
My perception of her fading was reality and her texting became more and more labored. I tried to set up another date and she cancelled. The fading continued. She ended up telling me that she wasn't ready for a relationship and gave me all the standard soft letdown things. I waited a bit and reached out to her again, trying desperately to rekindle something, but another couple of exchanges and she was once again, gone.
Pretty recently I was doing my standard purge of go nowhere women and I stared at her number for a few minutes. Fuck it, I sent her a text. Nothing, as expected. Two days later I deleted her number, something I had failed to do in so many purges before.
It's ridiculous because I know I barely knew her, but honestly it really felt like a loss. Like a relationship was over. I didn't get too sad or anything, but it had that same sort of unfinished business you always have when something ends. At that point, I was starting to feel as if I was actually ready for something serious. Nobody else had, or has to this day, come anywhere close to making feel like opening up to the idea of something true and lasting.
Date #22: Amy the Amazon
My general strategy in making a connection started off as tons and tons of messaging over the course of days and weeks, moving to text, then scheduling a meetup given the craziness of my first date. It evolved into a handful of messages back and forth, spread out over a few days, then securing the date and moving to text to iron out the details. When I met Amy, I was somewhere in between.
We chatted a bit straight away and moved to text pretty quick. She actually wanted to call me to "make sure all this fun would hold up in person." Of course, I passed the test with flying colors and we scheduled a date. Unfortunately, my schedule was full as usual, so it had to wait for a couple of weeks. During that time, I was pretty busy and not responding very quickly.
She actually called me out just before the date, saying she was going to cancel on me, but her friends talked her into giving me a shot. She needed more attention.
For the date itself, we settled on a nice Mexican place neither of us had been to before. She had trouble finding the parking garage I mapped for her, so I ended up meeting her on the corner, talking on the phone to find each other.
I knew she was tall, my height actually, but she was also big. Not fat mind you, rather thick and powerful. Former power lifter in fact. A true Amazonian beauty. Blue eyes, very dark brown hair just past her shoulders, and massive curves in all the right places. I'd later find out, a hint of abs. I stared at her shimmering black stretchy pants as I approached, her broad thighs and ass begging to suffocate me.
We hugged and chatted as we walked to the restaurant.
"You're not 5'11" I chortled.
"YOU'RE NOT EITHER!" she laughed.
We were both right. I round up a little and she rounds down... what I would consider a lot. She's just shy of 6' leaving a solid one inch between us.
Fun was had at dinner and we took a walk through the park. She was very sweet and fun and that potent physique had me intrigued. She informed me as the date grew late that she does not kiss on the first date, so I had to take her on another if I wanted that sort of fun. And I was interested in fun, maybe more.
Second date we joked about me not wanting to kiss until the third date and I even playfully denied her at one point as we took another walk riverside. Maybe 15 minutes later, we were making out. She was a good kisser and feeling her voluptuous body against mine was very arousing. We talked and talked, going on several more dates, but the timing just never seemed to work out for sexy time.
Eventually I realized that things were going to get serious and after my experience with Tina, I had my shields up. I wouldn't let her in. I told her as much and with a few tears, we parted ways.
