Reading old blog posts is such a bittersweet experience for me.. On one hand I love that I have a place to remember all of my dating “adventures” and even more important my “mid-adventures.” (Long time readers know what I’m talking about… some moments were just a total Jill created shit show… I mean “learning experiences”)

But on the other hand…

I get that really cringe,

like in vomit in your gut moment

when I reread blogs where I’m gushing over the people I’ve dated in the past (aka this dude , this asshat , or even this guy) …. The ones I really thought at the time were good guys and good matches.

Honestly, I’d rather send this failed selfie to 200 total strangers that have no idea what I look kind than reread those posts…

The reason these hit me so hard is because I had NO IDEA how GOOD it could actually get.

I met Dylan at a dinner with a group of new friends. When I walked into the restaurant he was at the door and introduced himself with a big smile. We sat next to one another at the table and it was literally like he was my best friend at the table.

On that first night he did thoughtful things like…

• Share his menu with me (asking if I was ready to turn the page)
• Move the same menu out of the way when I was taking my customary picture of my cocktail (to help get the look right for the pic and bonus points with no judgement )
• Slowly ate a single roll while I ate my meal that was delivered long after most of the table (he had eaten his large meal already but I told him I didn’t want to eat alone)

Doing all of these things… while engaging with the table (and drunk bar owner), genuinely laughing at my jokes, making me laugh and most of all being so open and free to me.

When I left that night, to be honest, I didn’t know what to think of it. It wasn’t that I didn’t find him attractive, he is honestly a smoke show, but I just hadn’t felt that secure with a man that quickly before. I didn’t know what it was but I liked it.

The next day, as the kids say “I slid into his DMs” and from that point on he took over. Giving me his number first and asking me out to dinner to a place I said I wanted to try a day or two later. It was just so easy…

Dylan’s and my first date was to a Louisiana Cajun food restaurant. The gumbo and tator tots were delicious…but the drinks.. oh the drinks .. yum… were to die for… Both of my drinks included a small voodoo doll, piece of candy and a sugar rim. Sweet and a little sassy.

Dylan would later tell one of my besties that he knew that night that he wanted to date me. He said it was because the way I turned around to the table behind us to chat with a young boy in dinosaur pajamas and his grandma. I even offered some of our untouched tots (that’s a real sacrifice).

Between you and me, I feel like he set the bar a little low. The kid had dark navy blue jammies with brightly colored dinosaur print.. I feel like discussing favorite dinosaurs is a natural transition for any human with eyes. But I accepted it as a win later on with my friend… because if a hot dude wants to give you brownie points for being human you just take it and feel the bask of the glow. No need to argue.

The next couple of dates included a very thoughtful and inside jokey Christmas gift on our second date (I had never gotten a gift so early on but I loved it), walking 4 miles in the cold to view giant wooden trolls (and more importantly cows), impromptu late night bonfires at a special spot next to a lake under the stars (with my fave beers and snacks) and many dinners and walks in the snow. The whole thing felt so magical and easy…

Now, in my previous relationships I have learned not to fall for a man based on his words but to pay attention to his actions. This was perfect for this relationship because I wasn’t vulnerable enough to ask him for words and he provided thoughtful consistent actions. But my lack of vulnerability did turn into me unilaterally pushing our relationship along. From the first time I said “I mean we are going to be exclusive, right?”, “I’m going to call you my boyfriend now”, “Put this date on your calendar as we are going (insert activity I’m pumped about here)” and most notably “I want to go on that road trip! Can I tag along?”

I was generous enough to give him time to answer my demands (clearly joking) but never really asked him questions about how he felt and the velocity the relationship was moving. I can blame this on being caught up in the moment, but honestly it was more about me not wanting to hear anything negative from him. I wanted to live in the easy version and focus on the actions…

One of the most important moments we had was when Dylan met my sister and her husband. It was a couple of months in and by that point I had been introduced to his family. We went out on a double date at a local seafood restaurant, again with GREAT drinks… (Quick side note I’m doing a sober November so clearly miss a good cocktail.. I’m sure there will be more). I had so much fun sitting there talking and laughing with three of my favorite people. Afterward my sister said, “holy smokes Jill! He is it! The way he looks at you and he finds you hilarious! Like actually hilarious!” To be fair, my sister and I find eachother pee on the floor funny, but we both know that not everyone shares our sense of humor. For Dylan to share it so genuinely was a big deal.

My favorite part of that night was when I got a little cocky and ate a whole dried habanero garnish on top of my drink. When I took the bite the dried powder inside exploded in my mouth… Like a literal firecracker. All parts of my being were on fire… I started with my water and then quickly moved to Dylan’s water. In the meantime, my sister is trying to get me to take a picture with her and keeps asking why my face is so weird. I am trying to smile and be normal but I am literally panicking on the inside. It was then Dylan stopped the waitress and asked for more water and if she had any milk. The waitress said she only had half n half and Dylan said “two shots please”. He later said he knew I was in trouble when I grabbed his water… I don’t normally drink water.

That instance characterized our relationship perfectly. He was always looking out for me. From asking privately if I want to leave a party when I hit “my wall”, to realizing I changed my mind about wanting candy for my purse before going to a party I was nervous about (and going inside CVS with me to buy it… even though I said I would be fine when we drove past and he asked me 5 minutes before), to insisting on driving during our road trip with very little sleep since the place we stopped at had 2 different kind of margaritas that he knew I would want to try.

It was always kind, always fun, and always easy. I was sure I had found the love that everyone told me about. The one who you look back and laugh at the idea of anyone else. There was no anxiety about our relationship (I just knew), no embarrassment (except when I farted for the first time in the car and immediately rolled down my window), and no hesitation from me to trust him. From going to adult prom, to late night Bubble Bobble playing, to tag teaming taking care of and engaging in conversation with my pets (and my made up stories about them), improving my house (painting my bedroom and sleeping on my old bed in the middle of the kitchen while the paint dried), and having a true partner to experience life with. There are literally a million stories that I could write about during that 6 months where my heart would flutter.

Then suddenly and quickly it turned hard. Dylan went through some large tough life events and pulled away abruptly. My hesitation to communicate when I was vulnerable and his tendency to isolate himself when things got hard created an unhealthy dynamic we couldn’t overcome. Then as the months went by our communication became less frequent, then business like and then non existent. I’m have no idea why when he started feeling better he didn’t come back. I have no idea how much of my memory is a reality and if I missed signs he was losing feelings. I honestly don’t think I’ll ever know (he’s now moved in and dating someone new), but this misadventure and experience has taught me a lot.

You may ask why I would write about something that I will most likely have that gut twisting cringe about later? It’s because I want to remember the magic, the ease and the feeling I had that 6 months. I want to remember the bar being so high and not accept less.

But most of all I want to remember that sometimes what makes relationships truly the easiest is asking the hard questions…

Also, let me add because I realize this will come up… I know it wasn’t just me that needs to learn from this experience but I am the only one I can control and know the full story to write about. Accountability is always on both sides.