Everyone’s got one but should your past transgressions cost you points on your dating record, or should we all be allotted a fresh start?
When I got the green light from my high school hottie to “come through” I hesitated. Hottie, or H for short, was a Dream Boat for many, myself included, and now, nearly 10 years after graduating and after weeks of some playful Insta flirting, he was finally giving me some type of play.
I can’t even lie; after H slid in my DMs inviting me out, I questioned whether the Dating Gods were playing a cruel joke on my dismal dating life’s behalf. Yet I shut down my mind and logic, whispered, “fuck it,” and quickly pulled myself together for a very impromptu date with H.
And I looked damn good. I usually like to have enough time to prepare both mentally and physically for a chance with someone as physically attractive as H, but luck was on my side (along with a few drinks) and I found myself hooking up with one of the hottest guys from my high school a decade later.
Things had definitely changed. In high school, I was your typical bookworm; quiet, shy, and I played in band all four years. Socially, I was an outcast while H was your quintessential star athlete.
So this hookup was not just a win for me, but for all the other awkward black girls in high school – past, present and future.
In any event our situationship moved forward full steam ahead; we continued hooking up.
Getting to know someone after such a long time is something I had never personally experienced. It was interesting. Luckily, H didn’t really know the awkward, ugly duckling and nerd I was in high school; he got to know the more mature and much sexier 28 year old woman I have become. That’s the Tiffani I always wanted him to know. As far as I was concerned my past wouldn’t come back to haunt me and fuck up whatever it was I was doing with Mr. Popular – or so I thought.
What I didn’t see coming was H totally blindsiding me with a breakup after hearing about a past hookup.
“The Asshole,” as I call him, is a guy I knew since adolescence. We carried on our “will they/won’t they” relationship for two years until I realized The A was never gonna “be” with me. As painful as it was to finally let go of the possibility of a committed relationship with him (and boy was it TOUGH), I willed myself into building back our friendship. Our broken “almostship” was on its last legs as we transitioned into this new space, and that is when H slid into my messages.
H had made it a point to tell me one night after a movie that he was not fond of “sharing,” especially when it came to girls his friends have been with. Even though The A and I were over romantically, our non-relationship/relationship was preventing me from moving forward. I thought I had finally left it all in the past, and H breaks up with me after The A clued him in on just how friendly we once were.
I was raw. I had never been dumped because of a past hookup. I can understand being dumped because you cheated, or for being a tad bit crazy or clingy, but this? I couldn’t deal. I was hurt because a) I wasn’t the one to tell H and b) I was being discarded because of a failed relationship. Haven’t we all had those? And I was fully prepared to tell H about me and The A, but our relationship was so fresh.
I am still having a hard time with being dumped because of my past. Everyone has one. Besides, isn’t the point of a #relationshipfail to learn from them so we become better partners down the line? How can we do just that if we are constantly being judged about who we’ve fucked and/or loved? Of course, our past relationships affect our present but how much should our past count when trying to move on and start fresh?
Things may have ended a bit sooner than I had hoped with The Hottie but this entire experience has definitely opened my eyes. And while I still am searching for the lesson in all of this instead of feeling completely slut shamed, there is one thing I can say for certain: no matter how this ended, this former, high school outcast hooked up with the most popular kid in school.
