January Jones & 14 Other Celebrities Who Dated 'Bachelor'/'Bachelorette' Contestants

The contestants on the reality series The Bachelor and The Bachelorette are in its own world. It churns out so many eligible bachelors and bachelorettes who are left to the wolves every week as they get kicked out of the house.

One has to assume that after being on a show like that would make it exceptionally hard to find love. You no longer know who is actually into you, who is trying to use the tiny bit of fame you have, and, of course, the tabloids are all over you trying to figure out how you are coping with going back to real life.

Some of the contestants on this show, however, actually achieve a level of fame that puts them on the radar of higher level people in Hollywood. They end up using this status to look for a rich spouse or to try and have a career in Hollywood of their own (with absolutely no talent). One of the better things that happens is watching them date around the Hollywood social scene. It’s quite shocking just how many celebrities have had relationships, dates, one night stands, and casual hookups with the stars of Bachelor nation. Here is a list of some of the more high profile celebs.

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15 January Jones

via People

For some reason actress, January Jones thought it was the greatest idea ever to accept a date request from Nick Viall. The pair seems pretty random if you ask us, and Viall didn’t have the best reputation on The Bachelor or The Bachelorette, so we have to wonder, what is his motive?

Twitter wasn’t having it when news broke that they saw the reality star with January Jones. To be honest, it’s a bit embarrassing for her, seeing as his reputation has been somewhat tarnished amongst the show's fans (which is A LOT of people). When Viall was asked by People magazine if he was dating after his very public split with Vanessa Grimaldi, he admitted to getting out there by simply saying, “I’m dating,” and “that’s about all I’ll say.”

14 Charlie O’Connell

via Stacker

Charlie O’Connell was already an actor when he auditioned for (and won) the role of the Bachelor for the seventh season of the show. So, he didn’t only date one contestant, he dated 16 of them. Unfortunately for him, it didn’t work out with any one of them. Luckily, he has now moved on and not given up on love. He’s an uncle to Rebecca Romijn and his brother Jerry O’Connell’s cute twins. O’Connell also chose Sarah Brice as the girl of his dreams but obviously, the couple just couldn’t find a way to make their love work. (No shade though, they actually did try to make it work. He didn’t propose at the end of the season as the contestants are encouraged to, though, but he did date Brice for several years.) They took a break and then tried it again but officially broke up again in 2012 and went their separate ways for good.

13 Shayne Lamas

via Reality TV World

The General Hospital actress and daughter of actor Lorenzo Lamas might have needed a boost in her career when she decided to be on The Bachelor in 2008. Currently, she is married to Nik Richie, but before he came into her life she appeared on and won the heart of British bachelor Matt Grant.

They quickly broke up, like literally a month after the finale premiered. Their relationship was swirling with rumors of infidelity which they both denied. She said that “she and Grant are still amicable and talk daily.” With all this behind her, she said that she kept the 2.85 karat ring and that Grant was fine with that decision. They have both moved on to new people and Lamas even has two kids with her current husband.

12 Evan Spiegel


Evan Spiegel's name may not sound familiar but his invention is something that almost everyone uses. He is the co-founder of Snapchat and is also an ex-boyfriend of Lucinda (Lucy) Aragon. She was on Juan Pablo’s season of The Bachelor, you know, the girl who was known as the “free spirit.” The self-professed hippie chick loves to be nude and was rumored to be dating Evan Spiegel even when she was on The Bachelor. She definitely was trying hard for attention on the show because she is actually a struggling actress, appearing on smaller shows like Comedy Bang Bang and trying to be the comedian on the franchise.

It gets even better though, she is BFFs with Kate Upton who was also rumored to have dated Evan Spiegel... Whatever happened to girl code?

11 Sarah Hyland

via YouTube

Wells Adams was on JoJo Fletcher’s season of The Bachelorette, but he only made it to week six. For Sarah Hyland, though, that was the best thing that could have happened. Not only did she want to be in a relationship that was healthy and stable, but she ended up finding it with a guy who actually seemed pretty genuine on the ABC dating show.

The actress told People magazine that she has actually been friends with Adams for a while and eventually (as naturally as possible), something sparked. The couple documents their relationship pretty heavily on social media and things look great; they seem to not be able to get enough of one another. Who doesn’t want a relationship like that? It also helps that he actually has a job that is legitimate: he is a radio host and has a podcast with Miley Cyrus’ sister Brandi Cyrus.

10 Ricky Hendrick


Before Emily Maynard was arguing with women on TV for the attention of one man, she was in a full-blown relationship with American Nascar racer Ricky Hendrick. And it wasn't  just any relationship, homegirl was engaged to this man, he is the father of her first child. Unfortunately, Hendrick died in a tragic accident, and while most people wouldn't be able to move on, she found the strength and moved on in a big way.

We all know that The Bachelor/Bachelorette franchise has a horrible track record with love. Let’s face it, out of however many double-digit seasons they have now, fans could probably count on one hand the amount of couples who stayed together. Maynard has been engaged four times and apparently the fourth time was the charm, because according to her it's the LAST time she will ever get engaged (whether it works out to husband Tyler Johnson or not).

9 Rodney Stuckey

Rodney Stuckey is a professional basketball player for the Detroit Pistons and also has a baby with Bachelorette contestant Cassandra Ferguson. She was on season 18 of the show and didn’t make it very far.

During the taping of After The Bachelorette, fans found out that she was back with Stuckey and trying to make her family work. Ferguson was with Stuckey originally and they met when she was a dancer for the Pistons, however, it’s hard being the girlfriend of a professional athlete. So, when that relationship went south, she appeared on The Bachelor looking for a new family. However, that rekindling happened way back in 2014 and by 2015 she was on Bachelor in Paradise. Now in 2018, it appears Stuckey has moved on; getting married and having another child with his wife. Hopefully Rodney and Cassandra can at least be civil for the child they have together.

8 Kris Jenner

Yes, the matriarch of the Kardashian family was once connected to Ben Flajnik. It was way back in 2013 when Kris had that random talk show. He was a guest and apparently, they hit it off so well that they got to dating. Their relationship reportedly turned romantic, and for a few months, he was apart of the most famous family in the world. (Lucky him.) Too bad he couldn’t parlay that into something more lasting for he too could be famous right now for doing little to nothing.

When Jenner finally did spill the beans about her relationship with Flajnik, well, it was apparently no big deal. She said there was no hooking up, they didn’t do the deed, and she just described them as “really, really good friends.”

7 Tomi Lahren

via twitter.com/Refinery29

Tomi is currently known for being the political activist that is annoying a lot of people with her ignorant and unresearched comments. But besides that, she was supposedly dating Chase McNary the former Bachelorette season 12 contestant.

McNary said to Us magazine, "We were talking for about two weeks, but we weren’t in the same place, so we went our separate ways, I have nothing bad to say about her. She’s a great girl."

McNary was JoJo Fletcher’s runner-up and proved to be a pretty great guy, so I could totally see why things wouldn’t work out with him and Lahren (she's kind of the worst). If he stuck around her, he would probably receive a lot of the backlash from her craziness or constantly be defending her on social media.

6 Sophie Monk

It’s safe to say that Sophie Monk is a pretty well-known name. She is mostly known for being a model but was able to somewhat transition into TV and film. She appeared in Click, Entourage, Date Movie, and few other things in addition to making the rounds on red carpet events. She was also engaged to Benji Madden of Good Charlotte. So, everyone was shocked when she showed up on Australia’s version of The Bachelor and WON.

She won the heart of Millionaire Stu Laundy. Immediately everyone assumed it was all for publicity, but the couple hung in there until they couldn’t stand each other anymore. They were caught on several occasions fighting in public and then making up very publicly. They have officially broken up for good by now.

5 Gerard Butler

via YouTube

Like Ben Flajnik, Courtney Robertson sure gets around. She has probably dated more celebrities than she has regular, non-celebrity people. This information was spilled in Robertson’s book, so one has to obviously question the validity of it. However, she listed her occupation as a model when she appeared on The Bachelor and that she was represented by Ford Models, which is a pretty well known.

The possibility of her dating all these celebrities is very real, but Butler hasn’t commented on his time with Robertson. She only glanced over it in her book because she probably had more popular celebrities (at the time) to speak on. However, she did have nice things to say about him, though, like, "he was so charming, when he looks at you it looks like he’s talking into your soul.” Sounds like a cliché, but okay.

4 Adrian Grenier

via E News

Here is another one for Courtney Robertson; she named Adrian Grenier in her tell-all book as someone she dated on and off. However, she admits that things never went anywhere because, as charming as Adrian was, "I didn’t feel a spark with him.” She then admitted that she just wasn’t interested. “Adrian pursued me on and off for the next six years!” During an interview on Watch What Happens Live With Andy Cohen, Cohen told Grenier that Robertson made a very favorable comment about his private parts. Grenier responded "I was just glad she got the size right!" He then “joked” and said, "and she’s seen a couple of them, huh." Yikes, sounds like a little bit of bitterness there. Let’s be honest, no credible celebrity truly wants to be linked to a reality star.

3 Jim Toth

via Marathi.TV/goodreads.com

Jim Toth is a Hollywood agent and has seen his fair share of gorgeous women. Of course, now, he is off the market because he is married to Reese Witherspoon. But, before he was married to her, he was linked to Courtney Robertson. Don’t worry unlike some of her other famous relationships this one did not end on a bitter note. "Jim Toth was thirty-eight, about thirteen years older than me, and ready for marriage and babies, the whole nine yards.” She said it was brief, but she learned quickly, "it was clear to me that we were in different places in our lives and he was too old for me.”

Her book was definitely an eye-opener, and something tells us that she has way more naughty stories to spill.

2 Jennifer Love Hewitt

Boy, Does Ben Flajnik get around! The Bachelorette star was tied to the beautiful Jennifer Love Hewitt in 2011. While what most people spotted sounded like a first date, it apparently seemed like it was going well. The couple obviously didn’t last because—fast forward to present day—Hewitt is married and a mother to two kids with a different man.

However, the two have very separate stories about what actually happened between them.

Flajnik has been reported saying they have hung out whereas Hewitt told Ryan Seacrest during an interview that "We did meet, but totally by coincidence." Yikes, it seems like she wasn’t trying to claim him at all; maybe they had a bad date, or maybe she realized that it looks kind of ridiculous for a celebrity of her status to be on a date with a man trying to make reality TV his career.

1 Jesse Metcalfe

via Glamour

Courtney Robertson was a messy chick while vying for Ben Flajnik’s heart on The Bachelor. She was one of the women that all the other women claimed wasn’t there for “real love.” It didn’t help that she ruthlessly told all the women, “I’m not here to make friends.” However, unlike many of the women on this list, Robertson was already making the rounds in Hollywood before she appeared on the popular show. Like many people who have no claim to fame, she wrote a tell-all book about her dating life and her time on The Bachelor.

In this tell-all, Robertson claimed to have dated Jesse Metcalfe, but Robertson said it didn’t work out because “Jesse needed a lot of reassurance." She went on saying, "I wish I could say that we were the greatest lovers since Christian Grey and Ana Steele. But I can't lie. The [deed] was pretty average.

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