My Pre-High School Dating Life

I was just a bit odd when it came to my early dating years. I freely admit that I’m going to be a bit embarrassed about recounting my pre-high school dating record but I feel that it may stand as a sort of monument to how strange one can be and yet still make it in the world of dating. I mean, I’m married now. Clearly I figured it out in the end.


It all began in fifth grade. I was just starting to really get feelings of admiration for the girls in my grade. I had liked a few girls before but not “like” liked them. There were fun to hang around with and play with.

Then my first ever crush was formed.

I was marching with my boy scout troop that day and tossing candy to the kids in the Fourth of July parade my town holds. It was seriously hot and I was already tired. Then I saw Emily, a girl whom I had known for a few years at this point, standing in the crowd. My heart skipped a beat and suddenly as if putting on glasses for the first time I saw her.

I was smitten immediately and quickly tossed a bunch of candy at her. I don’t think I knew how to handle the secrecy of it all, because my friends all knew very quickly. Maybe I wanted it to spread in the hopes that somehow it would set up situation for us to talk.

I remember that for the next few summers I would walk passed her house in the hopes that she’d be outside and we could talk. Granted, I was so gosh dang shy there was just no way I’d be able to get anywhere.

I remember giving her valentines cards and all that. Everyone in fifth grade knew I liked her. I bet even she did in retrospect.

Either way there was one day when I counted myself the luckiest kid in the world. We had a program for fifth graders called peer counselors. We would patrol the playground and report any sort of misconduct to the teachers or try to resolve it ourselves. It was a great program and I loved it. However, this day was special. You were always assigned partners to patrol the grounds with and today I got Emily as my partner.

We left lunch together and headed outside before the recess bells rung. I had been planning what to say for awhile and now was as good a chance as I’d ever get. The playground was absolutely empty, a rare sight to behold. She was out in front of me and turned around with a warm smile.

“Hey Emily.” I managed to eek out in my calmest sounding voice.

She looked at me and for that brief moment I held her attention. This girl who I had pined for was acknowledging me. Trust me, I was very young and this was a huge boost to my confidence.

As I opened my mouth to admit to her that I liked her, the recess bells blare. Kids came pouring out onto the blacktop and into the grass. Kids came stampeding out and destroyed any chance I had to admit my desire to Emily. It was a ruined opportunity I’d never see again.

Then came the end of the year when we would be transitioning to middle school. I really wanted to win the eagle award given out to a boy and a girl who were voted as the best model student of that class. I had a very proud optimism that my classmates had thought highly of me and my grades, so I was excited.

They announced the girl first, and had her come up. Emily rose and proudly walked to the front of the gym. I was sure that the stars had aligned and that a story book ending would be us coming together as eagle award winners.

The male award was next, and the teacher gets up to the microphone…


At this point I had already assumed I had one. In my little innocent heart, I believed in fate bring us together. I think I recall half standing at this point.


Within an instant I was utterly destroyed. All my hopes were dashed. Looking back, he was totally a model student (we were very close later in high school). I think that was the moment I learned that life will often not go as you planned. Glad this is the way I learned that one!


When I got to middle school I was introduced to a huge new wave of girls that I found very attractive. One such girl was Aurora. Unfortunately for me, she was very popular among the guys of our grade so I had a bit of competition.

Including my good friend Bert.

One day, randomly, Bert announces that he likes Aurora. This is obviously considered an act of war on my part, and the spiral of our then new friendship began to unravel. I think as some point I had strawberry milk spilled on me. Boy was I mortified. I think I was uninvited for a brief time from Bert’s birthday as well.

Luckily for us, I got over this crush pretty quickly when she moved away. Bert and I have since made up, yet I’m still plotting the ultimate revenge for all these transgressions. He’ll get what’s coming.


Now this is the first shortest of my relationships. It was honestly a bit of a mix up… so I don’t really count this as my “first girlfriend” but technically she was.

I was childhood friends with one of the girls on this list (Melissa who will be next) and she was good friends with Dana. One night the girls had gathered and were at a slumber party. Melissa gave me a call and began barraging me with questions.

Eventually she slipped in “do you want to go out with Dana?” I had been answering so many questions I must have misheard and said, “Sure.”

Obviously the next day when Dana had assumed we were then going out, things got a bit awkward. I think she tried to hold my hand before I realized what had gone on. It’s not that I didn’t like Dana as a friend, but I didn’t want to date someone who I didn’t like. Wouldn’t be fair, you know?


This one didn’t last very long. My childhood friend had always had an aura of my memories around her. I did think she was attractive and we both decided to give it a try. I think it lasted close to a week before we realized that we just liked two different friend groups.

Her group was always decently close to mine but the relationship was not going to work out the way we had hoped it would. Thankfully it was mutual so we broke up amicably.


Nicole was someone who I had just become aware of my eighth grade year. The reason that she was special was because she’s the first and only girl to ask me out and because she’d become my best friend Juan’s girlfriend for a huge part of high school. At this point, though she was interested in me.

I thought she was a good looking girl but to be honest I didn’t know her personally all too well. I remember she asked me out while walking with me between classes. The idea that a girl liked me enough to make the first move was all it took for me to say yes.

I recall my friend Simon had a crush on her, so he felt a bit salty at me for pursing her (really she pursued me!) Over the years Simon and I have grown close but this time period was rough for us, obviously.

If I recall we only went on one date together. I took her with a group of friends to a movie and we held hands. Oh man, that was a pretty cute memory.

This relationship only lasted a week. I’m not too sure who ended it but once again both of us felt the same way so it was an amicable break up. She and I remained friends for years to come.


“The Quad.” That’s how I met Tanya. This was one of the more fun memories I’ve had from my childhood. Let me explain how it happened.

I had a friend who went to camp with Tanya and he told me that this girl was very into Lord of the Rings. Say no more, I’m smitten already. We got each other’s AIM names and started to talk a lot. I mean we’d spend hours just talking about the most random stuff. She was really into Legolas and I admired Aragorn.

Eventually she told me that she wanted to hang out with me in person. She’d bring a friend and we could meet by a local mall. I was a bit nervous to meet someone whom I only met online (kind of through a friend but still). I recruited my best pal Juan to come with me on the journey to meet this girl.

So Juan and I got picked up by this girl, her friend, and her older sister. Holy cow did we have some fun. When we got to the mall, they ran across the street and nearly got taken out by a police car. Juan and I, being the brave heroes, jumped back and hid in the bushes until the cop drove off. Great first impression.

We were watching her sister’s school play Cats. One of the conditions for her picking us up was that we had to pick her up a Marble Mocha Macchiato Grande from Starbucks. We made a jingle that we still can sing to this day because we all thought it sounded so funny.

Tanya’s friend was Erika, and she was totally into Juan. We all hung out a few times that fall and began to call ourselves the Quad. We eventually got Juan and Erika to go out and I got to asking Tanya to be my girlfriend.

Well for some odd reason after we all started officially dating, we just got too busy to actually go see each other. I recall Juan’s break up was very messy with Erika. I was sure they’d never be on good terms again (they haven’t talked since so who knows!)

As for Tanya and I… well this is strange. I have no memory of ever breaking up with her. I think the fact that we lost contact for like five years sort of implied it? But honestly we never officially broke up. Sorry Tanya, I’ve dated other girls and even got married while we have been going out.

Funny continuation on this, though. I rekindled the friendship my senior year when I saw her on Facebook. I think I hung out with her a few times and had some great stories to tell about how things have gone since eighth grade. Still no break up.

Then when I was in college about three or four years ago, I got an email from a random girl in class asking if I was Dezz. I had a small Youtube channel going at the time and thought it was a fan of that. Nope, turns out it was Tanya! We hung out again and caught back up again since we both randomly met in our online statistics class.

Since then I’ve added her on LinkedIn where we’ll occasionally say hi. She said she’ll be in the states next winter. Maybe I can meet up with her and finally see if she recalls us breaking up.


This is the girl I consider to be my first girlfriend. I met Ali in my eighth grade homeroom class and thought she had a very cutesy aura about her. She had a way of talking, laughing, and moving that just captivated me. I was enthralled with her and wanted to get to know her better.

Once again, using the best tool I could, I added her on AIM. We began to talk a lot and eventually I learned we were very compatible. After a lot of time and some conspicuous hints from her friends, I asked her out by playing jeopardy on AIM.

Lame, I know, but that was super romantic. If only in my mind.

It went something like “Let’s play jeopardy! There’s only one category and it’s Ali. This guy wants to go out with you.”

Of course that guy was me. We dated for a long time and she was my very first kiss. We were at a mutual friends party and had been trying to get shy me to kiss all night. I mean she at one point dragged me into the forest to look for something. Clearly I was missing hints like no ones business.

Well eventually after some fun getting Juan to kiss a horse blanket, we got ready to leave. A dare earlier had said I dare you to kiss Ali. I leaned in and there it was. I remember it fondly, I was very excited up the rest of the night.

Eventually Ali likely grew bored with me. In all honesty, I don’t blame her. I never pushed the boundaries and she was someone that wanted to match her intensity. I remember she broke up with me by telling a friend to tell me. That one hurt a lot. It lasted about half a year, so to suddenly find out you’re single again through a friend was painful.

I think at some point we ended up dating again but I didn’t find her to be the same girl I liked. I broke up with her while laying under my bed, but of course the second time wasn’t as bad.

We ended up becoming very close friends and consider her one of my better friends during high school. I don’t talk to her as much these days because we’re both so busy, but I remember her fondly.


This one actually goes back a bit further than a few of these but I wanted to put her here since really I dated her in high school (may write up my high school dating life in another post). I’ll just include the parts that are important for that story here because they happened in middle school.

Becca was a very intelligent, athletic, good looking girl and I grew very fond of her during the seventh grade. At this point, I had “dated” some other girls but the one I truly felt for was Becca.

I had Juan over and we were talking to her over AIM. I think I had a bit more bravery thanks to Juan, but I typed “I have a confession. I like you.”

For awhile we both thought she was just going to ignore it because that seemingly came out of no where. I mean, we rode the same bus and got to know each other for awhile but never had I made any sort of desire known.

After a few more hours of back and fourth, she said, “I have a confession. I like you too.”

Man, I could have jumped over the moon at that point. I was legitimately about to faint from pure happiness. Nothing could have made me come down from that moment.

“But I don’t want to date anyone until high school.”

Oh, alright. That seemed like a fair, level-headed statement. I was a bit crestfallen as I thought I was going to be able to go out with her then but I knew that if I played my cards right, I’d be able to go out with her eventually.

Well I dated a bunch of girls in eighth grade, as I’m sure you’ve read. Most of them were short enough, but Ali and Tanya were pretty serious. Yet I knew after the dust had settled, I had learned from my experiences enough not to screw things up with Becca. Man, I wonder how she felt seeing me date those other girls. Am I the baddie?

Well either way I still felt the same way about her when eighth grade was coming to a close. Don’t think I forgot about what she said for even a minute. That feeling was unlike anything else. I had a great friend, Ben, to talk to about how things were going. He was a very popular guy but always had time to talk to me. Nothing changes, I see. He’s still wildly popular and still finds time to talk to me. Great guy.

Well Ben and I liked Becca and her friend. We were of course shy as all heck and knew they may overhear us at some point. We called them Shelob and the Witch King so that no one would understand who we were referring to. Obviously not because we thought they were evil, but mostly because when we’d see them we’d have to know quickly.

Some of my other friends took to calling our crushes “hint hint’s” for the same reason.

Well the eighth grade formal was coming up and it was like a miniature prom for the kids to have before going to high school. I was single and ready to ask Becca to the formal because I wanted a strong base going into high school. Ben also wanted to ask his girl, but for now he was going to help me.

We went out to my play set and dialed the number. I remember her dad picked up and when I asked for Becca I was shaking. Thank goodness one doesn’t have to talk to a girls parents before her these days.

I asked her to go with me to the formal. After a moment of consideration, she agreed. The over the moon feeling I had before was back in full colors and I cheered for at least twenty minutes with Ben. He managed to ask the girl he liked and she also agreed.

That dance was unreal. It was the first time I got to be close to Becca since we both admitted our feelings for each other. I was smitten. You could have seen the hearts in my eyes right then and there.

That laid the foundation which would alter my freshman year of high school immensely. At this point, we were not going out quite yet. To find out what happened next, you’ll have to see if I post my high school dating life. As if I need more of a reason to embarrass myself.

Overall, I’d say that the girls I dated were all wonderful. I didn’t have a harsh break up that left me unable to talk to one of the girls I dated again. I’m still able to talk to every one of these girls and have no bad memories (aside from Melissa but that is a whole different social dissection we can get into. I don’t even know where that went weird but it did. We went to a baseball game in high school with a mutual friend and didn’t even say a word to each other.)

Of the girls I listed above, the one I’m still decently close with is Becca. Her husband is a great friend and we always laugh about the old days when we meet up. At this point, I had not yet met my wife! She was two grades below me and across the country. I don’t think we could have met quite yet.


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