First, let me put the disclaimer out there. I'm a walking throwback. I live for 90s/2000s nostalgia, so I'm hoping to trigger a little bit of nostalgia for you. My next disclaimer is obvious or something you already know if you frequent these posts… I’m somewhat of a hopeless romantic. Even when I was a young girl, I was here for these couples (or their stories at least)! I loved them together and maybe even went through a bit of mourning when they broke up (or I mourned their broken love stories). To me they all seemed perfect for each other, but in the thick of things, they just didn’t pan out. Now, let’s get to the list.
India.Arie and Musiq Soulchild
If you are or were a neo-soul lover, you know that this couple could have been considered neo-soul royalty! Individually they were my favorites in the neo-soul genre because they both gave off a sense of calming confidence (that was simultaneously soothing). I was super excited when I heard they were dating! To me, they were literally gender counterparts of the other. Imagine my disappointment when I was minding my business being nosey one day and came across the story that they’d called it quits. There were not details (or at least I don’t remember any)—just that it was over.
Tom Green and Drew Barrymore
These two gave a new meaning to “match my goofy”. The first time I saw them together, I wondered… “why?”, but the more I saw them interact, they seemed to be the perfect amount of goofy and outlandish for one another. These 2 appeared on Saturday Night Live (of course), movies, and events together. They seemed to be enjoying each other so much that the people around them had no choice but to enjoy them too. They made it down the aisle, but things just didn’t work out (although I read somewhere a few months ago that they secretly married again). They divorced after a short marriage citing irreconcilable differences. This left us quirky hopeless romantics more than a little disappointed.
Usher and Chili
I won’t lie. Initially, every woman was jealous of Chili and complained that she was too old for Usher. I didn’t have a super strong opposition to the relationship (although I had a crush on Usher), but I thought it was definitely a strange match-up. Over time, videos, and several paparazzi pictures later, we all were sold. They were adorable together and the age difference wasn’t obvious. They were cute and “wholesome”. Our hopes were high—sky high. Then it happened… the break-up and Usher’s best-selling album to date—"Confessions”. Usher spent the entire album man-splaining his infidelity and we were invested! We needed to know what he’d done to “our girl” (fickle, I know) and if he was apologizing for it. To be honest, our heartbreak fueled his career and poor Chili was stuck looking for love with her mile-long list of deal-breakers. It was definitely a messy break-up and one that disappointed the fans. They’d seemed so perfect for one another!
Common and Erykah Badu
This relationship was undoubtedly built on an earthy energy vibe. Before anyone knew these two were dating, it was apparent that it would be likely to happen. It just seemed like it was supposed to “go” (like two puzzle pieces snapping together). Not only were they gorgeous together, but we got the neo-soul love song of a lifetime from it. So many people use “Love of my Life” (to date) as a wedding/reception playlist song because of the perfect energy they created making it. That was their relationship—perfect energy. They were together and then one day the were just—not. At least that’s how it seemed for me. I wondered where the perfect energy had gone, but accepted it. At least we’d gotten a beautiful love song out of it.
Justin Timberlake and Britney Spears
It all started at the Mickey Mouse Clubhouse… okay maybe not, but that was a strong coincidence. Both of these talented singers started there and somehow ended up dating. I will never forget those horrible matching denim outfits that convinced us that they HAD to be in love. There was no way any couple NOT in love was wearing those outfits (and on the red carpet, no less). We loved them for that amongst other things! They were “goals” for us teeny boppers and they were entertaining together! Eventually, news of the break-up hit everyone and Justin’s following single, “Cry Me a River”, insinuated Britney had been less than faithful to him. Eyebrows were raised everywhere, but no details were dropped. I’d just like to believe that the insinuation was to make the single a hit, and it worked. *Alexa, play Cry Me a River*
Lenny Kravitz and Lisa Bonét
These two were sexy rebels and the public was here for it! They seemed perfect for one another because they were weirdly rebellious. They both had this new-aged hippy vibe that was so cool and different at the time. They seemed very fluid and carefree. These two married rather quickly and were very public. We also got Zoe Kravitz out of the deal (let’s not forget that). However, it was rumored that they got together by cheating on their current partners. (Well if that doesn’t preface relationship turmoil…) While they seemed to have been perfect for one another, it was said that Kravitz started having affairs on Lisa soon after his career popped. I guess it was sexy (and seemingly perfect) while it lasted.
These are my throwback picks, but who do you think would make the list today?