Online Dating Just Got a Lot More Intelligent

How did Kristin Cavallari meet her new boyfriend?

We're truly living in a digital age because TikTok is the reason Kristin Cavallari was introduced to her new boyfriend Mark Estes. She told her best friend Justin Anderson that she was scrolling down her timeline when she came across what she called a "boy group" called The Montana Boyz and they both agreed one of them specifically is her type. She said, "He's gorgeous. Like, everything about him is perfect. But, he's also outdoorsy and manly."

Three weeks later, she got a DM from The Montana Boyz that said "I love you" and she immediately let them know she wanted to have them on her podcast. Although the podcast didn't happen, Kristin Cavallari appeared in one of their TikTok videos. Once Kristin Cavallari learned from her assistant that they were planning to move to Nashville, she arranged for a line dancing meet-up with The Montana Boyz and her staff. After they met, Kristin decided to call the guy who would become her boyfriend "Montana." (Cavallari uses Montana as a stand in for her boyfriend's real name during the podcast recording as she never names anyone explicitly on her show.)

Kristin Cavallari hard launched her new relationship with boyfriend Mark Estes on Instagram in February, and the rest is history!

How does she feel about their age gap?

Kristin Cavallari didn't know how young The Montana Boyz were, but she wasn't interested in pursuing a relationship with "Montana" at first. She did admit she had a brief issue with their age gap, but decided that "Montana" being 24 while she's 37 doesn't really bother her. Justin pointed out that she actually used to say she wouldn't date guys who were only 30 because she thought they were too young. However, she's more interested in who "Montana" is as a person and notes that life experiences and how you were raised is more indicative of one's maturity level than age alone.

Do Kristin Cavallari's kids like her new boyfriend?

Kristin Cavallari said her boys were so excited to meet "Montana" for the first time and she feels like they really want her to be happy. "I've been really good about separating my dating life from their [life]," she said. Her oldest son especially approves of "Montana" and it's shocking to Kristin because he's usually the toughest judge of whoever she's dating.

How has her career prepared her for public opinions about her relationship?

Kristin Cavallari is at a point where doesn't really care what anyone thinks about her new boyfriend. She's lived life in the public eye and is comfortable enough with herself to make decisions that make her happy. Kristin said, "...when this news came out, it's the first time in my entire life I 100% haven't given a sh-t what anyone thinks... My own mother is noticing a difference in me."

Did she mention anything about her divorce from Jay Cutler?

Kristin Cavallari and Jay Cutler were married for seven years before announcing their divorce in 2020. She didn't go into detail about it during the podcast episode, but she did talk about the magnitude of her relationship with her new boyfriend. "It's the first time I've gone public since my divorce," she said.

Everyone will always have opinions about a relationship they're not in, but all that matters is Kristin and Mark's happiness.

Where did Kristin Cavallari and her new boyfriend recently go during their date night?

Kristin Cavallari and her new boyfriend Mark Estes were spotted enjoying a fun date night over the weekend. Page Six notes they were seen exiting SUGARFISH — a sushi restaurant — in Beverly Hills. The *hot* couple was sporting ear-to-ear smiles and were holding hands as they strolled down the sidewalk. Mark Estes wore a more casual look while Kristin Cavallari rocked a slightly oversized cardigan, white tank top, and sleek leather pants.

TMZ also shared a clip of the happy couple that confirms who we think Mark Estes reminds us of too — the late actor Heath Ledger. It's the chiseled jawline for us.

How did Mark Estes feel about his first date with Kristin Cavallari?

Don't let his good looks and magnetic energy on TikTok fool you because Mark Estes was a bundle of nerves during his first date with Kristin Cavallari. He made the cute admission to Page Sixand even shared why Krisin Cavallari made him so nervous. He said, "Obviously she’s gorgeous. She’s an amazing person as well, and a great mother. So, yeah, pretty much [the] full package."

How is Mark Estes adjusting to being in the public eye with Kristin Cavallari?

Mark Estes may be in the spotlight because he's dating Kristin Cavallari, but that doesn't mean he's super enthusiastic about it. E! News caught up with him at the CMT Awards and he said, "It comes with the territory, I guess...It is what it is." One thing his friend Kade Wilcox — another one of The Montana Boyz — mentioned is that Mark is quite the romanticist when it comes to Kristin Cavallari. He told the outlet, "He's pretty good at date nights."

How does Mark Estes really feel about his relationship with Kristin Cavallari?

Kristin Cavallari's boyfriend Mark Estes recently appeared on Watch What Happens Live With Andy Cohen where he opened up a little more about his relationship with Kristin Cavallari. Andy asked the question everyone is wondering: is this a real relationship?

Mark Estes nodded his head and said, "Yeah, it's as serious as serious gets."

Problematic Message: Love is the most exciting when it’s forbidden.

Even if you haven’t seen the romantic comedy, you’ve definitely seen the GIFs: Andrew Lincoln, playing Mark, professing his love for Keira Knightley’s character through handwritten signs, one of which reads the famous line, “To me, you are perfect.” Yes, it’s ultra-romantic — until you look a little closer. “Although we all love an honest display of love, making a play and expressing your love for your best friend’s wife is not a good start for a relationship, on or off screen,” Tcharkhoutian says.

And the most harmful part of these fictional narratives is that they only show a fraction, if any, of the fallout. “This is a toxic dynamic that devalues the dignity of marriage and romanticizes the idea of being in love with someone who is ‘off-limits,’ without portraying the harsh realities of this kind of basis for a relationship,” Tcharkhoutian explains.

Problematic Message: A relationship that began with ulterior motives can become healthy and functional.

There’s no denying that Kate Hudson and Matthew McConaughey are a dreamy pair, but in this movie, their relationship is a nightmare. Their quick rise to love is certainly entertaining, but the foundation of their relationship makes it impossible to exist outside of fiction.

The two meet as means to prove themselves at their respective jobs, and in true rom-com fashion, their supposedly real feelings take off from there. Tcharkhoutian cautions against this behavior in real life. “This can set up a relationship to be something in which a person is objectified as a vehicle to help you meet your needs, instead of a mutual union and partnership with pure and honest motives of loving each other through thick and thin,” she says.

Lucy and Jack in "While You Were Sleeping"

Problematic Message: Falling in love with the idea of someone can result in a happy ending.

No one can resist a Sandra Bullock romantic comedy, so it’s no surprise this movie is still revered as a classic of the genre. It has all the necessary components: an unrealistic plot (she saves a man’s life, is confused for his fiancée by his family, and then falls in love with his brother while he’s in a coma — like, come on!), a handsome boy-next-door lead and, of course, love. However, much like the relationship in How to Lose a Guy in 10 Days, the foundation is faulty.

Falling in love with the idea of someone, as Sandra Bullock’s character does, doesn’t equate to falling in love with the actual person, Tcharkhoutian clarifies, and to start a relationship with this basis in real life is ill-advised.

Problematic Message: True love lies in the next adventure, which is far from your hometown and your past relationship.

Who hasn’t dreamt of traveling to a foreign country; staying in a cozy, remote cottage; and falling in love with someone even half as good-looking as Jude Law? Well, there’s a reason it’s a mere fantasy. Tcharkhoutian describes the phenomenon in The Holiday movie as escapism — the idea that you need to escape from your day-to-day life to find true happiness or, in this case, true love.

Although it’s fun to dream, if taken too far, this particular romantic comedy mentality can lead to irrational expectations. “This escapism mentality can create a false belief that international [relationships] are sustainable in the long-term,” Tcharkhoutian remarks. “True healthy relationships survive and thrive in the everyday, mundane routine, not in the exciting international adventure that depends on thrill and distance.”

Which rom-com couples stay together?

However, there are PLENTY of romantic comedy relationships we love! Some of our favorites include Nick and Rachel in Crazy Rich Asians, Matty and Jenna in 13 Going on 30, Harry and Sally in Meg Ryan's When Harry Met Sally, Elle and Emmett in Legally Blonde, and Peter and Lara Jean in To All The Boys I've Loved Before.

Lea Michele as Rachel Barry

Without a doubt, the most notable thing Lea Michele has done since the end of Glee is FINALLY starring as Fanny Brice in Broadway's Funny Girl. It was a super meta moment that brought reality and Glee lore together, and the entire internet lost their minds. You can also watch her in Scream Queens and New Year's Eve. Lea is currently expecting her second child with husband Zandy Reich, and has been very vocal about her struggle with PCOS.

Corey Monteith as Finn Hudson

Before he was on Glee, Corey Monteith had roles on Smallville and Supernatural. He's also reportedly the inspiration behind Taylor Swift's "Mine" from Speak Now. You can also see him in Monte Carlo and Final Destination 3. Corey passed away on July 13, 2013.

Chris Colfer as Kurt Hummel

Chris Colfer is one of my personal favorite members of the cast of Glee, especially since Kurt is such a sweetheart. You can see him in Absolutely Fabulous: The Movie and RuPaul's Drag Race: All Stars, and you can read his The Land of Stories book series! The actor and author has been in a relationship with Will Sherrod since 2013.

Jane Lynch as Sue Sylvester

Jane Lynch is one of the most iconic members of the cast of Glee thanks to her portrayal of Sue,and since the show wrapped, she's been involved with a number of other hit projects. You can see her in The Marvelous Mrs. Maisel, Wreck-It Ralph, Selena Gomez's Another Cinderella Story, and Only Murders in the Building. The actress lives with her wife Jennifer Cheyn, who she married in 2021.

Jenna Ushkowitz as  Tina Cohen-Chang

Jenna Ushkowitz joined the cast of Glee after her run in Spring Awakening on Broadway. She's done a few other Broadway shows like Waitress, and won Tonys for as a producer on Once on This Island and The Inheritance! You can also see Jenna in Lady Gaga's "Marry the Night" music video, as well as Katy Perry and Nicki Minaj's "Swish Swish," and listen to her And That’s What You Really Missed podcast, which she co-hosts with Glee star Kevin McHale. Jenna married David Stanley on July 24, 2021 (Kevin was her "man of honor" — cute!!) and in June 2022, gave birth to their daughter.

Kevin McHale as Artie Abrams

In addition to starring in Glee (and listening to his And That's What You Missed podcast, of course), you can see Kevin McHale in Bratz, Zoey 101, and American Horror Stories. He's been in a relationship with actor Austin P. McKenzie since 2016.

Ali Stroker as Betty Pillsbury

Ali Stroker was a finalist for The Glee Project (a reality show that gave contestants the opportunity to appear in the show) before guest starring in season 4. Since the 2013 episode, Ali has starred in Lifetime's Christmas Ever After and also had a small role on Only Murders in the Building. The actress also became the first person with a disability to both receive a Tony nomination and award for Best Featured Actress in a Musical for portraying Ado Annie in Oklahoma!

Dianna Agron as Quinn Fabray

After playing Debbie Marshall on Milo Ventimiglia's Heroes, Dianna nabbed the role of complicated cheerleader Quinn on Glee. She's also had roles in Burlesque, I Am Number Four, Ralph Breaks the Internet, and The Chosen One. In 2022, Dianna finished her third residency Café Carlyle which is sooo giving Quinn Fabray.

Alex Newell as Wade "Unique" Adams

Alex Newell stole hearts as Unique on Glee, and since the finale, they've also starred in Empire and Zoey's Extraordinary Playlist, as well as Broadway's revival of Once on This Island and Shucked (for which they became the first openly nonbinary performer to win a Tony).

Melissa Benoist as Marley Rose

Melissa Benoist just starred in Max's Girls on the Bus (watch our interview with her here!), but she might be best known for the title role in The CW's Supergirl. You can also see her in Patriot's Day, The Longest Ride, and Whiplash. Like other members of the cast of Glee, Melissa starred on Broadway and made her debut as Carole King in Beautiful. After splitting from Glee co-star Blake Jenner in 2017, Melissa got remarried to Chris Wood in 2019 and gave birth to their son in 2020.

Chord Overstreet as Sam Evans

My personal favorite project from this Glee cast member is Falling for Christmas, which also stars Lindsay Lohan! You can also see him in iCarly, The Bold Type, and The Middle. The actor and singer dated Emma Watson in 2018, and in 2020, Chord released his song "Hold On," which has over 826 million streams on Spotify.

Jayma Mays as Emma Pillsbury

In addition to being a part of the cast of Glee, Jayma Mays has starred in Paul Blart: Mall Cop, Heroes, and Red Eye. She married Adam Campbell in 2007 and gave birth to their son in 2016. Most recently, Jayma starred opposite Amy Adams and Maya Rudolph in Disenchanted!

Amber Riley as Mercedes Jones

Amber Riley's Mercedes is one of the best parts of Glee (and her rendition of "Bust Your Windows" is among the best performances on the show!!). Since the end of the series, Amber has starred in The Wiz Live!, The Little Mermaid Live!, and Monster High. She won Dancing with the Stars season 17 in 2013, and released her RILEY EP in 2020.

Darren Criss as Blaine Anderson

Darren Criss won an Emmy in 2018 for his role in The Assassination of Gianni Versace: American Crime Story, which is only slightly more impressive than his involvement in the viral, deep-cut production of A Very Potter Musical (kidding!). You can also see him in Melissa Benoist's Supergirl and Muppets Haunted Mansion. Darren married his longtime girlfriend Mia Swier in 2019, and the couple welcomed their first child in 2022.

Blake Jenner as Ryder Lynn

Blake Jenner starred in The Edge of Seventeen with Hailee Steinfeld and Haley Lu Richardson, as well as Supergirl and What/If. Blake married Melissa Benoist while they were both in the cast of Glee, but the couple divorced in 2017. In 2019, Melissa revealed in an Instagram video that she's a survivor of domestic violence + injuries she received from a past partner. Blake responded in 2020, revealing he had been the partner Melissa referenced.

Dot-Marie Jones as Coach Beiste

Not only does Dot-Marie Jones play a coach in the cast of Glee, but she's also a 15-time world arm wrestling champion IRL. You can see her in Lizzie McGuire,Material Girls, Weird: The Al Yankovic Story, and Killing It. Dot-Marie has been married to Bridgett Casteen since 2013.

Naya Rivera as Santana Lopez

Naya Rivera's Santana was one of the best characters on TV, and she had incredible vocal chops to boot. You can see the actress in Step Up: High Water, CSI: Miami, and Even Stevens. Naya passed away in 2020 while boating with her son Josey in 2020.

Heather Morris as Brittany Pierce

After you've binge watched Glee (again), you can see Heather Morris in Santa Fake, Cora Bora, Raven's Home, and So Help Me Todd. She competed in season 24 of Dancing With the Stars (she was also a backup dancer for Beyoncé, slay!), and shares two children with husband Taylor Hubbell.

Matthew Morrison as Will Schuester

Matthew Morrison has been in a number of musical productions outside of Glee, including the OG Broadway casts of Hairspray,The Light in the Piazza, and Finding Neverland. Most recently, he starred in Christmas movie Paris Christmas Waltz. Matthew shares two children with his wife Renee Puente.

Harry Shum Jr. as Mike Chang 

Harry Shum Jr. starred opposite Nina Dobrev in Love, Hard on Netflix, and you can also see him in Step Up 2: The Streets and Step Up 3D, as well as Everything Everywhere All At Once. He plays a small role during the credits of Crazy Rich Asians, and will reportedly star in a spinoff about his character and Gemma Chan's Astrid. He shares a child with wife Shelby Rabara.

Mark Wayne Salling as Noah "Puck" Puckerman 

Before joining the cast of Glee, Mark Salling starred in Walker, Texas Ranger, Children of the Corn IV: The Gathering, and The Graveyard. He also released his Pipe Dreams album after founding Pipe Dreams Records. Mark passed away in 2018.