An underrated part about being an athlete is scoring some magnificent dates. Even if you’re not the best looking dude, you can still earn points based off your fame in the sporting world. Just ask Charlie Villanueva who’s not the most GQ worthy athlete, yet he managed to score a rather lengthy relationship with the stunning model Michelle Game. There seriously is no greater example than that.
In this article, we examine some of the world’s top tier athletes and hookups they likely regret letting go of. All ends will be examined in this article, we’ll take a look at brief hookups these athletes encountered along with lengthy relationships, what they all have in common is the regret these athletes likely felt once it was all over. Who knows how many of these 15 have actually moved on?
From Tiger’s adult star romances to soccer star Neymar’s smoking hookups, we feature 15 steamy hookups these athletes likely regret letting go of. Enjoy the article and like always, be sure to share the article with a friend. Also, let us know via Facebook which athlete is likely regretting letting go the most!
15 Tiger Woods – Holly Sampson
Oh yes, he’s back! Tiger has made his return to the PGA Tour and fans couldn’t be happier. Whether you like the guy or not, the sport of golf is a better place with the legend on tour.
Of course, his personal life took a beating due to several affairs he took part in during his prior marriage. Among those he slept with was a couple of adult stars, one we imagine he might regret letting go was one Holly Sampson. Unlike some of the others, Sampson was nothing but positive recalling the encounter the two had. Holly put on a striptease for Woods on his birthday along with two other gals. Following the act, Woods would request Sampson come to his room and yea, you know where it went from there. Holly stated that the “session” was “amazing” and that Tiger had a smile the entire time, which is pretty awkward to think about.
14 Neymar - Caroline Belli
When it comes to scoring goals on the pitch, Neymar is thriving at the moment with PSG. Though in truth, he’s been terrific throughout his career not matter which jersey he's worn. The same can be said for his love life off the pitch as well, looking back at his dating/hookup resume, not only is Neymar one of the top womanizers in football but you can say he’s one of the very best among athletes altogether, yea his track record is truly that impressive - dare we say even better than Ronaldo’s? Cristiano might have the edge on the field but in terms of picking up, Neymar might get the leg up ever so slightly.
Caroline Belli is a perfect example of Neymar’s prowess with the ladies. She’s a stunning busty blonde that’ll have you drooling through her pics. She’s got 675 K followers and you’ll understand why once you look at her. How Neymar let this chick go, we’ll never know!
13 Usain Bolt – Kasi Bennett
Living life in the fast lane, it appears as though Bolt has got the same mentality off the track when it comes to his relationships with the ladies. Bolt has scored with a slew of stunning women, even most recently several publications ran stories pertaining to Bolt hooking up with two smokebombs inside of a Jacuzzi. What was alarming about the story is the fact that Bolt had a relationship with Kasi Bennett, though given the recent rumors, we have reason to believe that might be over sooner rather than later.
It’s a darn shame cause Kasi is hot as hell itself. The two were spotted partying together throughout the summer, even enjoying some extra time with one another partying it up on a luxury yacht. Down the line, Bolt will likely letting go of such a gem.
12 Michael Del Zotto – Lisa Ann
Yup, even hockey players have regrets with the ladies and perhaps, it doesn’t get any worse than the Michael Del Zotto incident as he was shamed publicly by multiple stars in the adult industry. Lisa Ann took to Twitter voicing her displeasures against Del Zotto claiming the hockey player wouldn’t stop harassing her for dates with her fellow adult colleagues. The rumor mill indicates that the two hooked up and Del Zotto would ask Lisa for others to join in on the fun – this lasted for two years according to the adult star.
She was alone either, Amber Rayne also took to social media confirming the story claiming he did the same with her. If Del Zotto could go back in time, surely he’d do things differently and just keep his mouth shut.
11 Nick Young – Iggy Azalea
This incident was so much worse than some of the others on the list given the fact that this wasn’t just a hookup and in fact, a serious relationship between Nick and his smoking ex Iggy Azalea. Of course, we all know by now how the story goes, in one of the most baffling and embarrassing incidents to take place on social media, Nick Young was caught being a cheater through the wonderful world of Snapchat. Yes, this is real-life and not some cheesy reality show. Although D’Angelo Russell was a world class moron in the incident, ultimately he wasn’t the cause of the breakup as Iggy admitted she even saw Young cheating on security footage, yikes!
Without a doubt, looking back at the situation, Young will always regret letting this relationship slip away.
10 Tom Brady – Adriana Lima
It’s hard to believe Brady has any regrets given the fact that he’s got a smoking wife nowadays in Gisele Bundchen, however, looking back at his history, he might be having some sleepless nights thinking about his past. According to the gossip mill, Brady briefly hooked up with Adriana Lima back in the days, who’s one of the most smoking hot Victoria Secret models on the planet. She’s also a monster in the fashion industry with a cool net worth of $10.5 million, yup, she’s truly got it all going for her and likely, Tom is dreaming of those days.
Lima would stay in the world of sports getting hitched to Marko Jaric, a former NBA player. After seven years of marriage, the two split last year in 2016.
9 Jarret Stoll – Paulina Gretzky
Like others on the list, Stoll has moved on nicely nowadays as he’s happily married to the stunning Erin Anders as the two recently tied the knot. Andrews is stunning and we applaud the former NHLer for locking down such a marvelous creature. Though, there is a "however" in this case as well and that comes in the form of Paulina Gretzky!
Yes, the two were in fact hooking up back in the day and given Paulina’s massive fan base, many were likely envious of the Kings former centerman. The hooking up would eventually end and Stoll would later pursue a stunning Playboy and SI model, Rachel Hunter. Give the guy some props, he’s got game! In the summer of 2017, he put his hookup days aside marrying Andrews as we stated. Not too shabby of a resume, though he’ll be having some sleepless nights recalling those days.
8 Lewis Hamilton – Kendall Jenner
When you assess both quantity and quality, nobody does it better than Lewis Hamilton who’s arguably got the best game when it comes to the ladies. Let’s take a moment to assess some of his past flings shall we. The list includes the likes of Rita Ora, Rihanna, Gigi Hadid, Nicole Scherzinger and most recently, Winnie Harlow. Yup, we weren’t kidding when we said the guy’s got game, like Bolt, he loves to live life in the fast lane even outside of his domain.
Another smoking hookup he’s likely dwelling over even with all these spectacular past relationships is his time would the beautiful Kendall Jenner. The two were spotted together by the paparazzi on various instances, though neither confirmed the relationship as an actual thing. Whatever the case might be, he’s dreaming of her still and likely the others as well. How can you let go of Nicole Scherzinger!
7 Matt Kemp – Rihanna
Although the breakup took place a couple of years back, we have reason to believe the Braves Outfielder is still living in regret after letting the stunning Rihanna slip away from his grasp. The two had previously dated in 2009, though they would separate a little later as it’s believed that priorities and time constraints put an end to the relationship.
Kemp might not have fully recovered since as he isn’t linked to anyone nowadays. Rumors were swirling back in 2013 that he was hooking up Khloe Kardashian, though nothing would come of the situation as it was said to have been a brief fling between the two. From Rihanna to Khloe, we can give the slugger some props on getting done with some high profile ladies. Though in truth, that doesn’t make up for the sleepless nights he’s likely having!
6 Chuck Liddell – Jayden Jaymes
UFC stars love to live the party life as well, just ask Conor McGregor who continues to party it up since his fight with Floyd. We wish Conor the best however as rumors indicate he’s been spiraling a little as of late. Get it together McGregor!
The same “get it together” sentiment was likely felt by the legend Chuck Liddell back in the day during his hook up time with adult star Jayden James. Things got so hot and heavy between the two that Liddell actually considered getting engaged to the adult star, though he would later break it off once things soured between the two. According to Liddell, Jaymes was only interested in the relationship due to the fact that it enhanced her reputation and made her gain fame with the masses. Leaking vacations pictures of the two, Chuck ended things though he likely shed a couple of tears beforehand.
5 Mike Comrie – Hilary Duff
Poor Mike Comrie. Not only was he forced to retire back in 2012 due to reoccurring hip injuries but he also broke things off with the stunning Hilary Duff. This relationship was a lot more than just a hookup, the two married in 2010 though in 2014, the couple would file for divorce as Duff was labelled as the one to end things between the two. Just imagine, you lost your smoking hot wife and career. That’s truly a WTF just happened type of moment.
Things went from bad to worse for Comrie as he was alleged of raping a woman. Though thankfully, the charges would be dropped. In a weird twist, the two were recently spotted together enjoying an innocent cup of coffee alongside one another.
4 Cristiano Ronaldo – Irina Shayk
Take one look at Irina Shayk and you’re probably going to be thinking, “what the hell was doing breaking up with this smoking chick”. As a matter of fact, Irina was the one to end the relationship after rumors swirled around pertaining to Ronaldo being unfaithful. It wasn’t the first time either as even model Natacha Rodrigues claimed he’s still being unfaithful nowadays with current partner Georgina Rodriguez.
In any event, as you might imagine, Irina moved on and she did so in a big way getting into a relationship with Hollywood Superstar Bradley Cooper. The two recently welcomed in a child, Lea de Seine Shayk Cooper, now that’s a long name...Even though he is Cristiano Ronaldo, he’s got to regret letting such a beauty go.
3 Alex Rodriguez – Melissa Britos
In terms of top MLB players that hookup with stunning women, A-Rod and Jeter are neck and neck looking at their pasts. A-Rod has got the way with the ladies, not only is he dating the marvellous J-Lo, but he also had a long-term relationship with the stunning Torrie Wilson, a former WWE Divas and one of the hottest in the company’s history which is certainly saying something.
Another one of his tremendous hookups, one of the low key nature was with breathtaking model Melissa Britos. According to the speculation, A-Rod was obsessed with this hookup and if you get a glimpse at the stunning babe, you’ll understand why. It’s truly hard to believe A-Rod would have sleepless nights given his smoking girlfriend nowadays, though Britos still has the power to make him feel such a sentiment given the fact that she’s a true smokebomb.
2 Michael Phelps – Megan Rossee
Phelps is another high profile athlete that loved to play the field, key word, “loved”. Nowadays, he’s happily in a relationship along with welcoming his first child into the world. He’s in a different place nowadays though beforehand, he loved to date and casually hookup. One of his finest hookups/relationships took place with the stunning Megan Rossee – an actress and you guessed it, model.
The two would end things in 2012 and many were shocked as the couple appeared to be a perfect match. The split was amicable and youth was said to have been the main reason for the separation. To his credit, Phelps did the right thing by ending the relationship and putting himself out there as a single bachelor, perhaps he should have given the same advice to one Tiger Woods.
1 Lamar Odom - Khloe Kardashian
Again, this one was a lot more than just a hookup. Odom and Khloe instantly clicked and got hitched back in 2009 after just a month of dating, yikes. Odom was well aware he needed to put a ring on it ASAP. Of course, the wedding was a huge hit on reality television and the couple would even get their very own spinoff in the reality world.
That was all the good but in the fall of 2015, the very bad took place after Odom was hospitalized and was put on life support. Making matters worse, he was picked up by medical responders at a brothel type of environment. Credit Khloe who waited for after his recovery to file for divorce – surely, Lamar’s living in regret thinking about how he let his ex-wife slip away.