The Shady Side Of Colton Underwood

Content warning: The following article mentions domestic abuse and drug abuse, and references suicide. 

"The Bachelor" franchise has spawned a lot of reality stars over the years, but only some of them have been able to remain in the spotlight long after their season ends. It's safe to say that Colton Underwood is one of those people considering that his life after the show was perhaps even more interesting than his time on TV. 

But Underwood wasn't always just a headline fixture — the Indiana native actually began his career as a professional football player. It was in 2018 when he found TV fame on Season 14 of "The Bachelorette," where he competed for Becca Kufrin's heart. From there, Underwood went on to do a brief stint on "Bachelor in Paradise" before he himself became "The Bachelor" for the show's 23rd season. During this time, Underwood had gotten a lot of attention for being a virgin but had hoped to find his wife on the show. He even told "Good Morning America:" "That's what I'm looking forward to the most, is getting engaged and then getting married shortly after that."

After a dramatic season on "The Bachelor" that included him literally jumping over a fence, Underwood chose Cassie Randolph. Although the two didn't get engaged, they had a very public romance followed by an even more public breakup. Underwood then shocked the "Bachelor" universe by coming out as gay. While that was a brave thing to do, many felt he'd done a lot of sketchy things since becoming famous. So let's break down that shady side of Colton Underwood.

Cassie Randolph didn't get her happy ending on "The Bachelor" when she got chosen by Colton Underwood, since they ended up having a traumatizing breakup. While their split had first seemed amicable, People reports that Randolph accused Underwood of "subtly engaging in a tactic that peppers in aggressive comments" on Instagram after he bashed her for talking about their split on TV. She then claimed that he tried to make money off of her by adding a chapter about their breakup to his memoir without her permission.

However, things really escalated when Underwood allegedly began stalking Randolph to the point where she filed a restraining order against him. According to E!, part of that filing read, "He has sent her unsettling text messages, repeatedly called her, and placed a tracking device on her vehicle to track her whereabouts." If that's not shady enough, he was reportedly seen by her brother standing outside of her bedroom window at 2 a.m. He was also seen by other family members and neighbors hanging outside her home on different occasions. 

What's more, per the filing, "​​Underwood admitted to his roommate and his roommate's girlfriend ... that he goes on multiple walks a day to Ms. Randolph's apartment building." With that said, it's not surprising that Randolph would be frightened enough to take legal action. Underwood however, was said to have initially downplayed the ordeal, with a source telling Us Weekly at the time, "This was all a surprise. He was completely blindsided."

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

Colton Underwood didn't just stalk Cassie Randolph but sent her disturbing and threatening text messages too. E! reports that Randolph included screenshots of those texts in her restraining order filing against the former "Bachelor" star. In one text, Underwood wrote, "Your [sic] a selfish person," and in another wrote, "You hid things from me and been so shady." He also accused Randolph of leaving him for her ex, texting her, "I'm just ... wondering if the woman I'm madly in love with is having a good time with her ex."

According to Extra, Underwood also texted Randolph about who was going in and out of her apartment to presumably make her feel that she was being watched by him. He even once allegedly threatened her because of it, writing, "I am going to keep you accountable." Underwood didn't harass just Randolph either, since the court filings report that he sent troubling texts to her best friend and brother as well.

What may be the most shocking, though, was that Underwood allegedly went as far as to use "alias phone numbers" to bombard Randolph and her friends with more unhinged messages. The filing additionally stated, "Mr. Underwood also sent harassing text messages to himself pretending to also be a victim of the anonymous stalker." Underwood reportedly admitted to doing this at the time and may have later addressed it on his show "Coming Out Colton" too. That's because he said, via Page Six, "I put a poor girl through hell of my own insecurities."

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

In 2021, Colton Underwood came out as gay during a bombshell interview on "Good Morning America." While the former "Bachelor" star was praised by some for his bravery and honesty, others felt that he only did that for shady reasons, such as to divert the attention off of his alleged harassment of his ex, Cassie Randolph. The editor-in-chief of Pride, Raffy Erma, even told Variety, "We shouldn't be glorifying someone who has this history of allegedly stalking a woman." Underwood responded to that criticism by saying, "I never want people to think that I'm coming out to change the narrative, or to brush over and not take responsibility for my actions."

Others criticized Underwood for using his sexuality as a way for him to stay in the spotlight. The fact that he came out on national TV and then announced a Netflix series about it at the same time made many believe he just didn't have the best intentions. For example, one person tweeted (with a heavy dose of sarcasm), "Colton coming out and then announcing a Netflix special in what seems to be an attempt to bury the fact that he stalked and harassed his ex-girlfriend ... is just *chef's kiss* ... Good job, @netflix."

Underwood's own father also accused him of coming out for financial gain. That's because he told The New York Times, "Did he come out on TV for money? Sure. But who in reality entertainment doesn't leverage their life and put it all out there for money?"  

It appears that Colton Underwood has been caught lying on several occasions, but you could say his most famous fib was pretending to be straight to be on both "The Bachelorette" and "The Bachelor." Underwood admitted to Variety that he had hooked up with men before going on the show where he seemingly strung multiple women along. Some of them apparently caught on, since Hannah Brown told "The Michelle Collins Show," "I was like, 'Oh, well I just misjudged [who] I thought I was going to meet' ... trying to drop down the expectations. But it all makes so much more sense with just who he was."

Underwood didn't tell his ex-girlfriend, Cassie Randolph, the truth either, in that she found out that he was gay when he announced it on TV. His other ex, Tayshia Adams, claimed on the "Bachelor Happy Hour" podcast that Underwood had also lied when he said that he slept in sweatpants in the fantasy suite to not give her the wrong impression. She added, "I'm not the only person he should be feeling bad for, there was other women that were trying to fall in love with you and really putting their hearts on the line."

After Underwood came out, he told Us Weekly that Chris Harrison was the only person from "The Bachelor" franchise who reached out. Yet Elite Daily reports that Nick Viall and Ben Higgins revealed on separate podcasts that wasn't true, with Viall calling him a liar. Higgins explained, "I know of multiple people that did, including myself, including friends of mine, that reached out to him. So I don't know why he's saying that ... I don't know if that's a good headline. I don't know if it makes the rest of us look unsupportive or what."

Colton Underwood got a lot of heat for his Netflix show "Coming Out Colton" which documented him sharing his sexuality with the world. While that sounds like a positive thing, many people felt the show wasn't actually beneficial to the LGBTQ community. For example, he was accused of profiting off of a marginalized community, with one media reviewer positing that Underwood was trying to rehabilitate his image. It also apparently didn't represent the real hardships of coming out. An EW TV critic explained, "Underwood had a chance to tackle what he says prevented him from living authentically — but the show completely squanders that opportunity."

It seems that many viewers additionally felt that Underwood avoided discussing how harassing Cassie Randolph led to his coming out. Yet he said he wasn't allowed to for legal reasons. Because of all that, the show didn't necessarily portray Underwood as positive as he may have hoped. One reviewer claimed that Underwood was in a great position to use his fame in a responsible way. His coming out could have been a truly powerful moment, but the reviewer felt the chance was squandered and suggested that Underwood had some more maturing to do.

Underwood responded to the backlash on the "Call Her Daddy" podcast but appeared to be dismissive with people's concerns. "I see the criticism ... I know that people are upset that I have white privilege and I got a series after coming out," he said. Yet, he added, "I never wanted to compare my trauma to somebody else."

"The Bachelor" franchise may have made Colton Underwood famous, but that didn't stop the former pro-footballer from throwing shade at the shows and the people who appeared on them. It seems the first time Underwood did that was on Instagram Stories when a fan asked about the engagement ring from "The Bachelor" during a Q & A. That's because he responded, "I never actually got a ring. But when the time is right, I'll buy a nice ring with no strings on it."

Underwood took another shot at the franchise when Cassie Randolph went on "Bachelor: The Greatest Seasons Ever," and he blamed the show for making Randolph talk about their split. He told the "Reality Steve" podcast, "She just got completely taken advantage of and completely manipulated." He even said before that, "There have just been too many things ... that has happened for me to feel comfortable working with them on a professional level."

Underwood also bashed Hannah Brown specifically, in his book, "The First Time," writing, "She went off on the remaining four girls ... It was the beast in her, roaring and raging." He then came for Rachel Lindsay when he commented on Us Weekly's Instagram post about her being in a feud. He wrote, "Does she like anyone?" before commenting it wasn't his business. However, he added, "What is my business is the countless number of times she's spoke poorly of me ... Funny thing is I have never met her."

It appears that Colton Underwood had abused prescription drugs at one point in his life for very tragic reasons. The reality star revealed in his Netflix series, "Coming Out Colton," that he mainly had an issue with Xanax. The former "Bachelor In Paradise" star explained, "I was suppressing my sexuality so hard that I was taking medication daily to deal with depression and anxiety, and that made me a paranoid freak." Things apparently got so bad that Underwood admitted that when he "hit rock bottom," he decided to take "a lot of Xanax" one night in hopes that he wouldn't see the next morning. Fortunately, he still did. 

While Underwood had turned to drugs as a way to cope with his internal struggles, he shared on the "Call Her Daddy" podcast that he actually avoided alcohol all together for different but still very sad reasons. "I would not party. I slept through my own house parties in college and it's because I was afraid that if I got drunk I would be gay," he said.

All in all, Underwood may have done some shady things over the years, but it's clear he had been through a lot in life that made things very hard for him. Despite his past mistakes though, "The Bachelorette" alum has continued to share his story with the world, which may help others who are also suffering not feel so alone. 

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ by dialing 988 or by calling 1-800-273-TALK (8255)​.