The Lost Decade of Dating

by Just Juan
3073 views 16 min read

“You know, you’re like a crown jewel. You’re not going to end up with just any woman. God will make sure of that. But in between now and the time the right woman comes, you’re going to be hurt a few times.” – Cynthia Sanders

Baseball great Yogi Berra once quipped a famous line: “déjà vu all over again”. In his own words, he said it was a reference to Mickey Mantle and Roger Maris slugging back-to-back homers during their Yankee tenure in the 1960s. The truth of the matter is that he might as well have been talking about me. After all, it’s me sitting on the carpet of this palatial apartment writing about the end of yet another chapter in my checkered love life. And if we’re keeping count, this makes the 2nd time this year I’ve been in this position, having started the year with what happened in a Lawrenceville, Georgia Panera Bread. Tonight, as we dined at a Montgomery-area Outback Steakhouse in our first face-to-face meeting since I returned from the West Coast trip on Sunday, The Canadian Cutie revealed to me that she didn’t think we had a future together in a romantic context. She was very matter-of-fact about it and expressed her hope that we could remain good friends…a scenario I’ve typically stayed away from when romantic pursuits break down. And yes, the conversation did include the “lethal injection of rejection lines”. Again, if we’re keeping count, that makes 18 times I’ve taken that particular shot to the veins. As I’ve written in Triumphs & Tribulations over the years, the sulking feeling that accompanies those stinging words has definitely left me a different person every time…like a piece of me is chipped away every time it happens. Tonight was no different in that context. Nor was the eerily quiet 54-mile drive home: it felt the same way as that quiet, cold, and long 2-hour drive down I-85 in January. There is something different about tonight though. It hit a little differently than this circumstance normally has hit me in the past. More than any woman I’ve gone out with or been somewhat seriously involved with going back to a 6-month stretch in 2010, I saw a potential in her that gave me legit warm and fuzzies. She reminded me of that Jesse Boykins III track, “Amorous”…I wanted to give her more of me. To lose her with her kind heart, her incredible brilliance as a person, her nurturing spirit, and her aura is a tough break for me. And don’t get me started on the physical characteristics. Let’s just say that before I meet up with her, I literally have to give myself pep talks on not staring too intently when I’m in her presence…whether it’s her eyes, her chocolate skin, or any other of the notable physical features. She may very well be the most complete woman I’ve ever dated. Simply put, she’s definitely the kind of woman you marry and start a family with. It’s absolutely heartbreaking to know that I’m not continuing on with her. And so, here I am again, back on this carpet writing about another lost opportunity at love. I f***in’ hate this feeling. It sucks.

The ending of romantic pursuits concerning The Canadian Cutie means I’ll very much likely head into October 24th as single, not in a relationship for the 4th consecutive year. I don’t really anticipate anything materializing over these next 2 months. Hell, I may be too wounded to even go back to the drawing board right now. The ending of this dating situation also likely spells the end of my dating and relationship experience as a 20-something. There are a couple of other women I met on a stretch back and there seemed to be some mutual interest…in correspondence, at least. But, like I just wrote, this last one hit a little different…in a really tender spot. I think I might chill for a minute. After all, 2 times on this carpet in a calendar year is enough as it concerns writing about lost opportunities in love. If I’m being honest with myself though, this entire decade I’ve spent with a 2 in front of my age has been a wash in the area of dating and relationships. I took nearly a full year off from dating after losing Valorie Drew before I got back into the swing of things and I’m really no better for it, I can assure you that. Going back to the last days of Triumphs & Tribulations IV in September 2004 to tonight’s entry in Triumphs & Tribulations XIII, my love life has been an absolute disaster. Mama Sanders was right when she said I was going to be hurt a few times. I figured maybe 2, 3, or even 4 times…not an entire decade.

The Lost Decade of Dating. What can I really say? 37 first dates. 22 first date flameouts. 6 dating situations that progressed far enough where we considered ourselves an item. No dating situation or relationship lasted a year. I’ve seen it all and experienced it all over these past 10 years. For me, it’s disappointing…disappointing that I’m still nowhere close to being in a position to fly somebody’s grown daughter to Tokyo to have my proposal moment…disappointing that the money I have set aside in a special savings account has grown exponentially with the October 24th contributions under the “add money to this account if I’m not engaged on my birthday” mandate…disappointing that what I figured to be a 2-year bounce back from what happened on Halloween Night 2003 has turned into a whole damn 11 years…disappointing because love, unlike any other area of my life, has seemingly taken the form of a cat-and-mouse game: its elusiveness as frustrating as the housefly that has escaped my fly swatter’s reach the last 2 days and as heartbreaking as the 4 years I waited between the ranks of senior airman and staff sergeant in the Air Force, made worse by back-to-back years as the #1 nonselectee. If I decided to write in The Single Guy’s Perspective series the stuff I’ve written in Triumphs & Tribulations since September 2004, that entire series would easily be the most riveting read on this site.

So what has this decade been like, really? It’s been a mix of good and bad dates, relationships that seemed like dreams in the beginning only to end up as nightmares, and some careless errors on my part. I’m pretty sure there were at least 4 times I probably had someone special in my crosshairs but I failed to pull the trigger. To sum it up, it’s simply a lost decade. Where do I begin to unveil this madness?

THE 1ST DATE FLAMEOUTS. I mentioned that since I got back into the dating game after losing my first love to a fatal car accident on Halloween Night 2003, I’ve been on 37 first dates. We’re talking about from my time in Spain to Valdosta to Tokyo to the DC area to South Korea and here, in East Alabama. There were even dates when I went on vacation like that one time in Singapore or when I was deployed to Iraq or when I went on military business trips like when I went to San Antonio or to the Florida Panhandle or that one time in Okinawa. I probably shouldn’t count those but being a statistics guy, I guess it’s only fair that I do. Getting the 1st date typically hasn’t been much of an issue for me. I can talk—or more impressively, write—myself into a first date. Since 2004, only 7 women have declined even the first date. As a guy who was once the 14th most attractive boy in a class that only had 12 boys in 7th grade, I’ll take an 84% clip in this scenario any day. The issue, more or less, has been with follow-on dates. Of those 37 first dates, only 12 ended up with at least 1 other date. The other 25 were 1-and-dones with 3 of those being my decision. That leaves the 22 flameouts. Some were simply a matter of two people not clicking in a romantic sense. But there were some flameouts that left me a bit bewildered. There was the one woman from down in Valdosta that basically ended the 1st date because she felt I wasn’t giving her tatas enough attention. The way I remember it, her words were something like “I got on this dress, got these [tatas] out here for you and you ain’t even looking”. There was the one woman who used me and our 1st date as some kind of pawn in a chess game between her and her boyfriend. Apparently, she was mad at him and decided to go out with me to a restaurant that he worked at. He was literally our waiter. There were 3 women who were in it for the food and 1 who wanted access to the AAFES Base Exchange. A couple of the women refused a 2nd date because I don’t drink or club. In their words, I’m “kinda boring”. My height at 5’11” lost me 3 chances at a 2nd date as those women apparently wanted men who were at least 6’ tall…remember, the difference between 5’11” and 6’ is basically the length of a #1 regular paperclip. Aside from feeling like I was in a spin cycle when I had a stretch of 8 consecutive such dates, the first date flameouts don’t bother me too much. I’m a different kind of dude and though I can easily adjust to most the personalities of most people I deal with, it’s not as easy on the other side. For the most part, I’ve never taken the first date flameouts personally.

THE UNPLEASANT SITUATIONS. There were some bad dating situations over these last 10 years. My experience with The Instant Gratification Girl comes to mind. It was a classic Valdosta, Georgia romantic situation…a military guy and a college girl. We were set up for a Teedra Moses “Rescue Me” simple kind of love until she decided that waiting for me to realize my potential didn’t measure up to life as a drug dealer’s girl. There was The Aquarius from Augusta—who looked like a college version of Daphnée Duplaix—and how we trended good until her hatin’ ass best friend had her giving me the silent treatment, eventually leading to a scenario where she chose the friend over me. There was one woman who had been in a physically and emotionally abusive relationship before I showed up on the scene. We went on 2 dates and she decided to go back. Hopefully, that turned out a little better for her the 2nd time around. The Cocoa Goddess makes this list too. The 1st of 4 women I met on MySpace, she was a Georgia girl through and through…born and raised in the boonies of Middle Georgia. The biggest city she had lived in (Valdosta) happened to be the smallest city I had ever lived in up until I moved here last year. We actually started out as really good friends. In fact, she once had co-best friend status. We reconnected on the back end of my Tokyo assignment and once I returned to the United States in the Summer of 2010, we started officially dating. It was all good too…very, very promising. We went to see The Nutcracker at the Fox Theatre in Atlanta in December 2010. I presented her with a diamond pendant necklace at dinner afterward and I left out of her presence that night thinking that I would surely “be flying her to Tokyo in the summer for a marquee moment”. The next morning told a different story. She returned the necklace and said that though she cared deeply for me, she couldn’t do it. Nearly 4 years later, her words still sting: “I think I may love you, I really do. But all I want in this life is to be a Georgia girl…to be in love here, to be barefoot and pregnant here, cooking Sunday dinner with my mom here…and you have your dreams of your exciting life in far off places around the world”. She didn’t want to take that away from me and it hurt my soul. There was the whole thing with The Lovely Liberian. I met her with about a month left on the clock of the Joint Base Andrews assignment. We kept it close while I was in Seoul for a year and by the time I was knocking on the door of independence from the Air Force, we were actually trending towards entertaining something serious. But 2 weeks before I was due to visit her in DC, she revealed that she had a baby during the entire time I was gone. It wasn’t even about her having a baby as I think she may have conceived very shortly before we met…it was the fact that she didn’t tell me. Of course, there is the Miss Stillman College thing from last year, which still vexes me today. We were in a fantastic space in our dating relationship until she had that ridiculous dream that her friend interpreted, casting me in a negative light. I gave her a chance to come clean on why she really wanted out of the relationship during our sit-down in Panera Bread in January but she maintained a hard line that it was about the dream and premonitions and s***. As for me, I’ll go to my grave suspecting that the relationship was sabotaged because she was a Seventh Day Adventist and I’m a Nondenominational Christian.

THE GOOD ONES. Not all of the dating situations ended in an unpleasant fashion. There were a couple that were really good from end-to-end but for one reason or another, it just didn’t go any further. They still hurt but not as much as the unpleasant ones I just wrote about. The Woman of Peace comes to mind. I met her at a speed dating event in Tokyo: all Japanese women, all foreign men. She was Portuguese-Japanese and she looked more Portuguese than Japanese. Her name in Portuguese literally translated to “woman of peace”. We had a 5-week thing late in the Summer of 2008. It was really good actually until I brought her to the Japanese-American Friendship Festival at Yokota Air Base as my special guest. That was not well-received by some of the other Black women on the yard, in particular one who I had asked out twice only for her to decline twice. I remember her berating me about dating a White woman and her tag team partner accusing me of being on “some sellout s***”. The Woman of Peace, living up to her name, actually pulled the trigger on ending the dating relationship, saying “you have to work with those women every day and I don’t want you to fight them over me”. In hindsight, I wish she was more in tune with her Portuguese roots as opposed to her Japanese roots because I would’ve absolutely gone to war against all of those chicks over her. I crossed paths with The Bodacious Brit in December 2008. She was a London-born English teacher in the Aomori Prefecture who happened to be lost in Roppongi Hills, Tokyo. Guess who was her knight in shining armor (or maybe, the black bomber jacket)? We hit it off immediately. From emails to MySpace messages to subliminals on Facebook to me finally getting extended use out of that au by KDDI candy bar phone, me and her had great communication. It was a good 4 ½ months. I think we helped each other through a cold winter in Japan. We went to a couple of concerts together and even did the whole Daikanransha thing in Odaiba. She hosted me on all-date dates in Aomori and I hosted her on all-day dates in Tokyo. I’ll never forget how she managed to convince me to have a beach day with her in the middle of January…in Hachinohe. There was also the time where we hosted in our respective homelands: me hosting a weekend in Los Angeles and her hosting me in London. Unfortunately, that trip to London was the end. Her teaching contract had expired and she really wanted to focus on breaking into the film industry as a costume and makeup specialist so it was back to the UK for her. We had a great week in Londontown but I flew back to Tokyo without her. It was a good little thing while it lasted…kind of like a whirlwind-type thing.

THE ONES I SHOULD HAVE AVOIDED. As far as I’m concerned, there are 3 women during this 10-year stretch that I probably would’ve been better off avoiding though it’s debatable as to whether or not I’m in this exact position in life had I not met them. Let’s start with The New York Nightmare from Jacksonville. I met her on MySpace around the same time I met The Cocoa Goddess. Let’s just say that whole thing started bad and got progressively worse before ending horribly. If I had to call it, she was the worst girlfriend ever and in hindsight, I should’ve fled after the first meeting. She’s the center of one of those “mandatory flashback posts highlighting seminal moments in my life” that I alluded to in this blog’s open and if you want to know the top reason why I left the United States to go to Tokyo for 3 years, look no further than her. I have a special series of posts coming down the pike in October. I’ll probably cover more of her in one of those. There was The Curvaceous Capricorn. I met her on the BET Vibeline back in the Spring of 2006. Yes, yes, yes…I know. I actually used that service…the free version at least. I actually probably would have never entertained anything with The New York Nightmare from Jacksonville had The Curvaceous Capricorn not ghosted me the day before we were supposed to meet for the first time. When she did resurface, I was in a makeup-to-breakup cycle with The New York Nightmare and The Curvaceous Capricorn became something of a “port in a storm”. After the tragic events of February 2007, we did try to see what was in store for us but I was soon in Japan and that complicated things. She wanted much more out of me than I was willing to commit to from 7000 miles away. It didn’t help that she became impatient, got pregnant, and had a baby while I was away. When I was returning to the States in 2010, I offered to give it another go…even inviting her up for a week in DC. She declined and opted to try to make it work with her daughter’s father for, as she put it, “the baby’s sake”. From that point, it’s been something of a distance between us…not made any better that she married him a few months later or that we have this dynamic of me being the little girl’s godfather in the middle. There was The Community Planner. She was an intern in my unit at Joint Base Andrews and under normal circumstances, I wouldn’t have even entertained her…she was outside of the 3-up, 3-down rule. But being emotionally vulnerable coming off the whole deal with The Cocoa Goddess and some peer pressure from my colleagues factored into her and I seeing each other. We actually hit it off good and I even had a pleasant relationship with her son. Everything was good until she sent me a “we need to talk” text. And when we did talk, she had that unassuming tone I wrote about in January. I’ll probably cover all of this in a future post of The Single Guy’s Perspective but the long and short of it is her son’s father decided to come back and she said she wanted to give being a family a 2nd try, which meant I was out. The fallout from that resulted in me fleeing to South Korea in a series of events that still resonate even today.

THE ONES WHO GOT AWAY. Of course, there were some women who got away. For various reasons, I was hesitant to pursue, and with the benefit of hindsight, I now see that had I taken a chance with them, some special things probably could’ve happened. The first one that comes to mind is The West Virginian. I met her in the old Yahoo! Messenger chat boards back in late 2004. She was super cool, funny, and very attractive. We had great conversations on a wide range of topics. I loved to hear her talk. Her accent was intoxicating. There were 3 reasons why I didn’t pursue her: (1) she lived in West Virginia and I lived in South Georgia, (2) she was 17 though I wouldn’t have guessed that until she told me, and (3) she was literally a brand-new mother…having been late in her pregnancy when we met. We didn’t have any official dates but we had a great online friendship that included the occasional phone calls. We talked a lot about my life as a young airman and her life as a young mother. We were cool enough that I sought out her opinion on whether or not I should bolt for Japan in the aftermath of the whole deal with The New York Nightmare from Jacksonville. She was one of the most vocal on the side against me leaving. Her exact words were: “I don’t think it’s worth it…there are plenty of good women here and it makes no sense for them to pay for what another woman did to you”. In hindsight, maybe I should’ve taken her opinion a little bit more seriously. Maybe I should’ve also given her some serious consideration. She was far beyond her years when we met but the 27-year-old version of her today is a literal lottery ticket for some dude out there. In theory, I probably could’ve waited for her to come of age in the Spring of 2005. We’ll never know though. There was The Ghanaian from my time in Tokyo. She went to my church and we were amongst the handful of young, unmarried, and otherwise unaccompanied singles at my church. Because of that dynamic, we found ourselves hanging out from time to time. She was very friendly and she was always smiling. She was fantastic with kids…especially the babies. And if I’m being honest, I don’t know if there is a woman on the planet who looks better in a red dress. We went out once…a simple feel-out date. We basically ate at the Fussa McDonald’s and walked around the SEIYU, where I bought her a rose from one of the street vendors. As I was walking her back to her place, we almost got ran over by one of the church members, who turned really nosey in her inquisitiveness about what was happening. And of course, that member wasn’t one to keep a secret so when people saw us hug each other during the welcome at church the next morning, there were a lot of interesting eyes on us. I think, to some degree, neither one of us really wanted the spotlight so we kinda left it right there. A few months later, I thought better of it but it was too late. Another guy had swooped in and they eventually married. The Northwestern Wildcat is definitely one who got away. I was minding my own business on a Chicago “L” platform during a visit in June 2009 when she walked up and made small talk. It was one of those rare moments when I was the hunted and she was no doubt the hunter. She was a medical student at Northwestern University. We went out once during that brief 3-day trip in Chicago but we stayed in touch over the phone and through email as I went back home to Tokyo. There was definitely mutual interest but we couldn’t overcome the distance. Sometimes I do wonder how things would’ve turned out if she would’ve been willing to wait until I returned to the States the following summer. There was The Parisienne. I met her while I was staying in the NCR. She was French-born to Togolese parents but had been living in the United States for several years. Very beautiful and equally talented: I saw her do things with hair that I’ve never seen before. She and I had fantastic chemistry from the start…like first kiss on the first date chemistry, the only woman to hold that distinction. I definitely think she was into me but I was still in a rough place coming off what happened with The Cocoa Goddess and The Community Planner not to mention I wasn’t exactly sure of the dynamics of entertaining a serious relationship with a woman of her background: traditional parents, African roots, slightly older. I played coy somewhat but the South Korea assignment definitely sapped whatever could’ve been out of that situation. She moved on and eventually got married. There’s a lot of regret about that one. Last but certainly not least, there was The Californian. I also met her on Yahoo! Messenger…about a ½ year after I met The West Virginian. I remember her posting a @};—— in the chat board and me sending her a private chat, asking how she did it. She basically taught me how to do it and I always started and ended our Yahoo! conversations with an electronic rose after that. We had fantastic chemistry on the phone. She was really easy to talk to. And she was drop-dead gorgeous…the most alluring eyes on the planet. It was clear that we both had an interest in each other and I strongly considered entertaining possibilities but I ultimately decided against it because I didn’t feel comfortable with the distance…her being in Southern California, me in South Georgia. In hindsight, considering I ended up in somewhat of a long-distance relationship with The New York Nightmare from Jacksonville a year later, I probably should’ve just taken my chances with her. Like The West Virginian, she wasn’t a fan of me making the move to Japan but she wasn’t as vocal about it. We kept in touch for a few months after I moved to Tokyo but the deployment to Iraq pretty much wiped that out. We lost contact and I haven’t spoken to her since. All of the women I missed on were special but she may have been the most special.

So there you have it. The Lost Decade of Dating. I was really hoping I could break this cycle with The Canadian Cutie and move towards a special place but I guess Cupid had different plans. It appears that this streak of misfortune in the love game will extend into my 30s. In a Flashback Friday post 3 months back, I wrote about Seal’s “Kiss from a Rose” being the music track I’ll walk out to at my wedding. As I wrote then, those lyrics resonate with me and each time I come out on the losing end of this dating and relationships thing, the more I feel like “a greying tower alone on the sea”. It’s such a bummer.

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Lakeisha McMahan October 2, 2021 - 11:37 pm

This was most definitely a good read! Definitely not your average guy!! Thanks for sharing.

Just Juan October 4, 2021 - 3:52 pm

Thanks for reading.

CJ May 2, 2022 - 6:52 pm

Yo, this was very relatable to my experiences seeing as we were both Fly Guys aka Air Force.

I was laughing reading your statistian approach to the dating numbers so to speak!

Well done! Hua!


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