“If I Buy You A Ring, You Should Buy Me A Truck”—Why Dean Unglert From ‘The Bachelorette’ Is A Walking Red Flag

Women love to joke about the red flags they see in guys – sometimes things that are as harmless as wearing Crocs or hating ketchup. But if a man you’re interested in exhibits the same red flags as The Bachelorette alum Dean Unglert – run.

So what are Dean’s alleged crimes? At first glance, he just appears to be a nonconformist, a guy who enjoys the nomadic #vanlife so he can see the world and have new experiences. But there are some troubling aspects to Dean’s skepticism of marriage that point to damaging myths that many men and women believe.

Dean and fellow reality TV star Caelynn Miller-Keyes have been dating since they met on Bachelor in Paradise in 2019. Since then, Dean has been pretty vocal about his lack of enthusiasm for marriage.

“I made a deal with [Caelynn]. I was like, ‘I’ll buy you a ring, if you buy me a truck,'” he said in June 2022, sparking online backlash.

You have to credit Dean for one thing – transparency – because the statements like these that he makes on his podcast don’t exactly make him look like a gentleman. 

How Did Dean and Caelynn Meet?

Dean, 31, made his The Bachelorette debut as a contestant on Rachel Lindsay’s season in 2017. Caelynn, 27, made her The Bachelor debut on Colton Underwood’s season in 2019. But the two didn’t pair up until their time on Bachelor in Paradise (my personal favorite show in the franchise). 

Their relationship was a tad controversial – and not just because it was unexpected. Dean is an outdoorsy, caution-to-the-wind kind of guy, while Caelynn is a poised pageant queen. No one could deny the two had chemistry – but then Dean broke up with Caelynn on her birthday during their season of BIP. The way he did it was abrupt and rude, demonstrating that he really only had his wants and feelings in mind.

However, he later returned to the show (after she had spent time getting over him and moving on to a new, healthier relationship) to win her back. Although she had other options, Caelynn chose to leave with Dean. Couples on BIP are incentivized to get engaged at the end of the season, but Dean and Caelynn decided such a quick engagement wasn’t for them (probably the right choice – many Bachelor contestants have opened up about the fact that these engagements are often based on fleeting emotions). 

“It’s always kind of tricky coming out of the show right away because you're agreeing to date someone that you don't really know that well. And so for the first month or two or three, even, we're still learning a lot about each other and still figuring out if it's actually going to be a relationship that works,” Unglert told Us Weekly in 2020. “But once you kind of get past that initial difficult hump, everything got really, really good for us.”

The two have been going strong ever since. Caelynn even threw herself into van life with Dean before the two bought a house together. But throughout their relationship, Dean has taken heat for statements he’s made about Caelynn – including calling her “suffocating” – prompting her to come to his defense.

Symbols Aren’t Superficial – They’re Important

Dean revealed that he threw a “fit” while ring shopping with Caelynn on his podcast Help! I Suck at Dating (the two aren’t engaged as far as the public knows).

“I was like, ‘I don’t even want to be in here right now. I don’t really care what I wear on my finger’… We had a bit of a scuffle,” he said. “It’s such a touchy subject…Caelynn makes significantly more money than I do, and here I am having to spend all this money on something I don’t even want. Like, I want her to get what she wants, but she’s the one who wants to get married.”

Don’t even get me started on the fact that Dean often acts like he’s being dragged to the altar – but his conflict with Caelynn underscores a sad trend: Wedding rings have become a consumer item to “express yourself” rather than a sacred symbol. It also once again demonstrates that Dean only has his desires and feelings front of mind, pushing aside Caelynn's plea to get married.

Dean is totally right to steer Caelynn toward a ring he can afford – it’s been reported that she wanted a 4.5 carat diamond! – but acting too cool to care about wedding rings is forgetting that a ring symbolizes fidelity, commitment, and an eternal bond. It’s an embodiment of a husband's and wife’s vows that everyone can see. Ironically, Dean and Caelynn have said that they wear makeshift wedding rings to signal that they are taken to members of the opposite sex – so they at least understand that part of it.

“[Dean] started wearing a hair tie around his ring finger, just to fight women off,” Caelynn once revealed. “And I liked the idea. And then we just talked about getting rings. It’s just nice to know that we’re in a strong, committed relationship without necessarily having to get the government involved, as Dean likes to say.”

Viewing marriage as something that only affects the couple and no one else is a pretty new idea – such an individualistic attitude toward marriage developed in the West over the last hundred years or so. Sure, a marriage license is a piece of paper issued by the government, but a wedding ceremony isn’t just for the bride and groom. It represents the uniting of two families. One could even argue that gathering friends and relatives for a wedding ceremony is a way of asking them to hold the new couple accountable – solid marriages are the bedrock of a healthy society, and your wedding guests are witnesses to your promise to stay together for better or for worse.

Women Proposing to Men Isn’t “Equality”

Dean has famously said that he would rather Caelynn propose to him than vice versa.

“I've made it pretty clear to her. I was like, 'If you really want to get married, you should be the one proposing to me,' so I think she's got something in the works for that,” Dean said in November 2021.

Caelynn addressed the idea a few months later.

"The more I thought about it, the more I loved it, because traditionally, he would propose to me. That's something I've dreamt of for so long, and that's something that he doesn't get – a day that's catered to him and this special moment where he's really thought of. That's when I was like, 'Oh, my gosh, I love this,'" she said. 

There’s a laundry list of serious reasons why women should not propose to men – check out our breakdown here. But that’s not the only arena where Dean and Caelynn have wanted to upend tradition. They have said that instead of Caelynn taking Dean’s last name as her married name, they may both change their last name to Bell, Dean’s late mother’s maiden name. 

And going back to Dean’s truck for a ring comment, relationships are not purely about monetary exchange: If a man spends X number of dollars on a woman, that doesn’t mean she needs to do the same in the name of equality. 

Expecting the same things from men and women in a romantic relationship may technically be equal, but it isn’t fair. Women have shorter biological clocks than men, face more serious consequences from sexual relationships, and, by design, are more involved in caring for their children. Put simply, men have time to waste that women do not. 

If Dean and Caelynn truly want to build a life together, they’ll have to stop thinking in terms of dollars and cents. Married couples can’t compartmentalize his and hers finances – everything is supposed to be going toward the same goal. And especially if a couple is in it for the long haul, there may be seasons where the wife makes more money than the husband, and seasons where it’s the opposite. 

For many women, starting a family can be scary because they may be giving up income and becoming more reliant on their husband as they go through pregnancy, birth, and caring for an infant. That process can enhance a relationship, or ruin it if the couple doesn’t understand that a woman’s contribution to a household is more than just the money she brings in.

His Words Need To Match His Actions

“I am in the camp of I’d rather show Caelynn that I love her rather than say that I love her…Talk is cheap, more or less, you know, anyone can say anything, but what it boils down to in my eyes is action over words,” Dean said when he and Caelynn were first dating.

Normally, we’re told to make sure our actions match our words – but in Dean’s case, it’s the opposite. He is essentially living as a married man but can’t admit it…well, most of the time. Dean has said that he and Caelynn are “basically” married, according to Us Weekly. The two have even participated in a so-called commitment ceremony.

"[Caelynn and I] still have our separate accounts... but we have a joint account we both put money in for house stuff,” he added (the pair bought a house together in 2021).

Hmm…he’s skeptical of marriage, but he’s benefiting from organizing his finances like he’s married? It would be one thing if Dean and Caelynn still lived separately or didn’t combine their finances. But he's essentially enjoying all the benefits of being a husband without making a lasting commitment.

“Here’s the thing, in my opinion, I don’t need the title of husband to show the world that I’m committed to one person,” Dean said in 2020.

No couple gets together with the intention of breaking up, but it still happens. There are rough patches in every marriage, but both spouses know that they can’t just cut and run without consequences, monetary or otherwise. It’s not particularly romantic to think about, but legal marriage is a safety net for both husband and wife – and resistance to marriage in a long-term partner may signal deeper conflicts to come.

It's Not A "Green Flag" That You Won Him Over

Dean has said that Caelynn is the “most suffocating” woman he’s ever dated – an example of negging if there ever was one. 

He later clarified the comment: "It's a horrible word, don't get me wrong. It's the wrong adjective to use to describe anyone in a relationship. I was simply saying that in past experiences, I would hate to be suffocated, but with Caelynn, although my instinct is to say, 'Don't suffocate me,' in reality, I'm like, 'You can suffocate me because I enjoy spending time with you' sort of thing."

It’s no secret that women love to feel like they’ve “saved” or “changed” their boyfriend. Caelynn may consider it a victory that she was the woman who finally got Dean to settle down. But ultimately, relationships should not be about fundamentally changing your boyfriend or winning him over. Our egos often make us feel like a relationship is worth it because of small victories – “He’s never introduced a girl to his family before, but he introduced me!” or “He never says I love you, but he said it to me!” – when we should actually be asking ourselves what we’re getting out of the relationship.

Closing Thoughts

A relationship where one person has to force all of the progress is a lopsided relationship – and a doomed one. We don’t know if Dean and Caelynn will last a lifetime or not, but their public relationship provides lessons we can all use in our private lives. And if you spot a man with any of Dean’s red flags, you know what to do. 

Help make Evie even better! Take the official Evie reader survey.