The Dating Diaries

The Dating Diaries

Oh, my favorite question:

"Jamie, why & how are you still SINGLE?!" 

I am absolutely flattered by this question, but the answer to it is a mouthful and can get me going on a rant fairly quick. 

It's the post you've been waiting for friends:

Why being single and dating in your 20's is complete bullshit.

Please keep in mind as you are reading this, that this is MY personal opinion and experience with single life and dating. I am completely aware that everyone has their own experiences, journeys, and opinions. This just happens to be mine and I have every right to whine about it, as you have every right to decide to read it or not to read it. Respect. 

I'm just a Carrie Bradshaw looking for her Mr. Big... or more appropriately, her Aidan (he was always my favorite).

But dating has me feeling exhausted.

Yes, dating can seem oh so fun, exciting, new, and glamorous to those who are in relationships. "Oh, to be single and in my 20's again" is something I often hear from the older crowd. Sure, I'd love to be single and in my 20's during your era as well because today's society and generation has it all screwed up. 

I like to blame a big part of it on social media and the Internet. These things have been great contributors to the world for many reasons, but dating is not the best of them. What I would give to read a hand written letter, to get a phone call, or actually be told in person how he's feeling about me instead of reading it over text or getting tagged in a #womencrushwednesday post. (that's actually never happened to me, but you get the gist) Don't get me wrong, I'm not a total and complete hater of social media apps used for dating purposes - heck I've used just about all of them, but it definitely has stolen some of the excitement that should come along with dating. 

I understand I may be coming off as a bit of a hypocrite because the same reason why I'm annoyed at dating apps is also a big reason why I personally use them. Convenience. I've spent plenty of days/nights/weekends trying to meet men "organically" by putting on a fresh face of make-up, taking the time to find the right outfit, spending money on an Uber, and more money on drinks ( never actually had a guy come up to me and offer to buy me a drink on the spot) only to go home a bit disappointed because I didn't meet any suitors. Ladies, the same guys going out to the bars are most likely the same guys using the dating apps. Laying in bed with a comfy t-shirt, face mask, glass of wine and watching Sex and the City re-runs while swiping left and right not only saves me money but all the hassle and possible let down as well. It's the best of both worlds, am I right?

But conveniency can come at a cost. 

Social media has created a sense of urgency and demand in relation to dating and hooking up. Congrats 2018! It's now easier than ever to get laid whenever you want! But if you are someone like me who's looking for something a bit more serious this makes finding "the one" also harder than ever. 

Heres the Deal

Majority of the men in their 20's (at least the ones I continue to come across) want to party, let loose, and not be tied down to anything or anyone. I have a theory that a serious wake up call occurs when men make the transition from 29 to 30. Until then, they are usually dedicated to a number of things other than a relationship. 

Now, I know there are plenty of men in their 20's struggling to find the right person as much as I am. I'm not saying every guy in their 20's is a sleaze ball. But I believe there is also an art or science to dating that I just can't figure out. It comes down to a balancing act. Not making them your number one priority, but still keeping their interest engaged. Saying how you feel, without always talking about your feelings. Being honest, but not too honest. And the hardest balancing act of all is the fine line between being labeled as a slut or a prude. If you put out too soon, you're easy. If you make him wait to long, your a prude and he gets bored. I have always been one to make him work for it, but shit I'm by no means a prude either. 

I get it guys, why should you put effort into courting a woman and wait for the big pay off when you're one right swipe away from a different woman putting it out for free? 

My idea,


Then we can all be fucking prudes together and be proud of it!

But, who am I to judge other women who want to release their inner Samantha Jones?

Ladies should be able to have casual and easy sex as well. Not all women are looking for a serious committed relationship and I get that! But social media has made the convenience of no-strings-attached-sex even easier. The women actually looking for the strings to be attached, are getting the shit end of the stick. 

Just some of Jamie's bad, yet humorous dating experiences

The set up  

This was a blind double date that my best friend set up. The date went well - good conversation, flirty, and an innocent good night kiss after he walked me back to my car. We went on a second date to the movies, also went well! As we were texting and planning for a third date, he made it clear that even though he was into me, he wasn't looking for a relationship and just wanted to have some fun. 

Not that kind of fun buddy, two dates ain't workin' for it. We were obviously not on the same page. 

Jiffy Lube guy

So, I met him "organically" at good ol' Jiffy Lube. He caught my eye and if I see something I like, I go for it. Channeling Drake here, as I was in my sweatpants, hair-tied, chilling with no make-up on look, I walked up to him and gave him my number. 

Later that week we met for wine and we had a good time! I was about to order an Uber when he offered to drive me home, his car was a few blocks away at his place. I agreed and as we headed back to his place FOR HIS CAR, and he slyly invited me inside for a tour. Ugh. Sure enough, he sits sprawled out on his couch pulling the whole high school slouchy couch move on me to start an old fashioned make-out session that I was not feelin'. He then proceeded to climb up a steep ladder up to his loft and asked me to come take a look.

I'm not that easy bro.

I looked straight up and said "yup, its a loft". Annoyed, he made his way down and I looked him right in the eye and said, "I'm not having sex with you tonight and I'm ready to go home." So, he drove me home. I never heard from him again.  

The vino man

This was a Bumble date. He wasted no time in asking me out for drinks, which I admire. We had a wonderful date that ended as a double date when we met up with my friends. Friends gave me the thumbs up and he drove me home with a sweet kiss goodnight. 

For our second date we shared dinner and drinks at one of my favorite restaurants. He was a gentleman and paid for everything, walked me to my car, and was a very good kisser. 

We made it to date three and he, on his own, invited me to a soft opening of his new business. Seemed promising right? All signs pointed to interested. I met some of his friends and colleagues, grubbed on some food truck food, and had a great time. He then invited my friends and I to his Grand Opening later the following week. Cool, this guy is into me as much as I'm into him.

Two days later he told me I'm beautiful and a really cool person but just isn't looking for a relationship right now. I never replied. I embarrassingly called off the plans with my friends. 6 months later he was in a relationship... 

I was left confused. 

Short Pilot 

Another Bumble date. As soon as I got to the bar for drinks, I saw a guy waiting outside. Sadly, my initial reaction was, please don't let this be him.

It was him.

Nothing worse than a date you have to push through. He was bland, flew private planes for a living, but the connection was lacking. In all fairness, he looked different than his pictures... my biggest pet peeve. 

Mr. Bartender

You guessed it, Bumble again. We had plans to meet for drinks (my favorite first date activity) and he wanted to cancel because he ended up having to work. I decided to meet him at work while it was dead and continued with our plans. He poured me a glass of wine and we engaged in conversation. While talking it soon became evident we had nothing in common. He liked to backpack and camp, while I prefer resorts and glamping. He wasn't close with his family, which was a red flag for me. He also didn't like wine. 

He texted me wanting to meet again, and I pointed out the obvious. He agreed as well that we had very different interests but just wanted to try again anyways. 

Sorry dude, you're not getting this girl in a sleeping bag anytime soon. 

Semi Promising

For a number of reasons I'm not going to go into too much detail with this one. But I was the one who slid into the DM's and asked him out on a date. We dated for two months. There are a few note worthy stories I could write about but I'll leave you with this. 

After sleeping together, he turned off all the lights and opened his laptop. He asked if I wanted to watch a movie, it was a weeknight and already pretty late. I began to assume he may ask me to stay over (baby steps). As the movie began, lying there in the dark he said "I always fall asleep when I watch movies" (okay, my assumptions are looking promising) I laughed and he proceeded to tell me "So when I do fall asleep, you can let yourself out". Now, as I was processing what he had just said he followed up with "And don't turn on the lights when you do". 

This dude was being fully. Fucking. Serious. 

I looked at him and exclaimed that it was pitch black and I was naked. He turned on the lights, smiled, and said you can get dressed now. He legitimately had no idea (probably still doesn't) that I was fuming, the most oblivious man I have ever met. 

You bet I got fucking dressed, zipped up my jacket and walked the fuck out of there. He asked "wait, you're leaving?"

Yes, I'm leaving and don't bother walking me out. 

He didn't. It was over. 

In Conclusion

I do believe that dating has a lot to do with timing. Many would agree that timing is everything. Although it seems like timing has not been on my side, I'm sure one day it will appear that timing was indeed, always on my side. 

But until then, I'm in agreeance with Carrie Bradshaw:

I'm throwing the dating towel in for a bit and sticking to what I know best because ladies, a fabulous new pair of shoes never disappoints. 


the simple Rae



The Vegas Guide

The Vegas Guide