Skylar Astin, the charismatic actor who captured hearts as Jesse Swanson in the beloved Pitch Perfect franchise, has maintained a fascinating romantic journey that has fans and media alike. Born Skylar Astin Lipstein on September 23, 1987, this talented performer has navigated the complexities of love in the public eye, experiencing both the highs of marriage and the challenges of divorce.
The Broadway-trained actor, who originated the role of Georg in Spring Awakening before transitioning to Hollywood success, has been particularly notable for his high-profile relationship with Pitch Perfect co-star Anna Camp. Their real-life romance mirrored the musical chemistry audiences witnessed on screen, creating one of Hollywood’s most talked-about couples during the mid-2010s. However, Astin’s dating history extends beyond his famous marriage, encompassing relationships with fellow performers, entrepreneurs, and industry professionals.
As of 2025, fans continue to wonder about Astin’s current relationship status, especially following his divorce from Camp in 2019 and subsequent relationship with entrepreneur Lisa Stelly. The actor’s romantic timeline reveals a pattern of meaningful connections with accomplished women, each relationship contributing to his personal growth and artistic development. Understanding Astin’s dating history provides insight into the man behind the performances, showcasing his journey through love, loss, and the ongoing search for companionship in the entertainment industry.
Early Relationships and Broadway Years
Skylar Astin (Image via Getty)
Jessica Bridgeman (2008-2009)
Skylar Astin’s documented romantic history begins during his early career years with Jessica Bridgeman. This relationship lasted approximately one year, from 2008 to 2009, coinciding with Astin’s emerging presence in the entertainment industry. While details about their relationship remain relatively private, this period marked Astin’s first publicly acknowledged romantic involvement as his career began gaining momentum.
Lauren Pritchard (2006-2011)
One of Astin’s most significant early relationships was with Lauren Pritchard, spanning from 2006 to 2011. This five-year relationship occurred during crucial formative years in Astin’s career, as he transitioned from his Broadway success in Spring Awakening to pursuing film opportunities. Pritchard, also connected to the theater world, represented a partnership rooted in shared artistic passions and career aspirations.
The relationship with Pritchard lasted through Astin’s college years at NYU’s Tisch School of the Arts and his decision to take a leave of absence for his Broadway commitments. This partnership provided stability during a period of significant professional growth and artistic development for the young actor.
The Anna Camp Era: Hollywood’s Musical Romance
Meeting on Set and Early Romance (2013)
Skylar Astin’s most publicized and significant relationship began in 2013 when he started dating Anna Camp, his co-star from Pitch Perfect. Their on-screen chemistry as Jesse Swanson and Aubrey Posen translated into real-life attraction, creating a romance that would fans of the musical comedy franchise.
The couple’s relationship developed during the success of the original Pitch Perfect film and continued throughout the production of the subsequent sequels. Their shared experience in the musical comedy world, combined with their natural chemistry, made them one of Hollywood’s most beloved couples during the mid-2010s.
Engagement and Marriage (2016)
After three years of dating, Astin proposed to Camp in January 2016, marking a significant milestone in their relationship. The engagement represented the culmination of their shared journey through the Pitch Perfect trilogy and their growing commitment to each other, both personally and professionally.
On September 10, 2016, Skylar Astin and Anna Camp exchanged vows in what became one of the entertainment industry’s most celebrated weddings of that year. Their marriage symbolized the perfect blend of professional collaboration and personal devotion, with fans celebrating the union of two talented performers who had found love through their shared artistic endeavors.
Divorce and Separation (2019)
Unfortunately, the fairy-tale romance came to an end in April 2019 when Astin and Camp announced their separation after nearly three years of marriage. The couple released a joint statement confirming their decision to divorce, citing irreconcilable differences while requesting privacy during their transition.
Camp filed for divorce shortly after their announcement, and the proceedings were finalized by August 2019. According to legal documents, both parties waived their rights to spousal support and agreed to share ownership of their Los Angeles residence, demonstrating their commitment to an amicable separation despite their personal disappointment.
Post-Divorce Relationships and New Beginnings
Skylar Astin (Image via Getty)
Lisa Stelly Romance (2020-2021)
Following his divorce from Anna Camp, Skylar Astin found love again with entrepreneur Lisa Stelly in 2020. Stelly, previously married to media personality Jack Osbourne, brought her own successful business ventures and three daughters to the relationship. Their romance became Instagram official in July 2020, when Astin publicly confirmed their relationship status.
The couple’s relationship was characterized by public displays of affection on social media and mutual support for each other’s professional endeavors. Astin praised Stelly’s entrepreneurial spirit, while she supported his musical and acting projects. Their partnership represented a mature approach to blending families and careers in the entertainment industry.
However, the relationship faced challenges due to demanding schedules and geographic separation. Astin’s work commitments, including filming in Canada, created strain on their connection. In September 2021, after more than a year together, the couple announced their breakup.
Reflection on Post-Breakup Life
Following his separation from Lisa Stelly, Astin opened up about the challenges of single life in the entertainment industry. Speaking on the People Every Day podcast, he admitted that life after the split “gets lonely and it gets a little isolating.” His candid reflection revealed the personal cost of maintaining relationships while pursuing demanding career opportunities.
Current Relationship Status (2025)
As of 2025, Skylar Astin appears to be single and focusing on his career and personal growth. Following the conclusion of his television series So Help Me Todd in May 2024, Astin has been dedicating time to his music career, releasing several singles and exploring new creative outlets.
While his ex-wife Anna Camp has recently sparked romance rumors with stylist Jade Whipkey in May 2025, Astin has maintained a relatively private approach to his personal life. His social media presence focuses primarily on professional projects and personal interests rather than romantic relationships.
Lessons and Growth Through Relationships
Skylar Astin (Image via Getty)
Skylar Astin’s dating timeline reveals a pattern of meaningful connections with accomplished, creative women who have supported his artistic endeavors while pursuing their own professional goals. Each relationship has contributed to his personal development and understanding of love, commitment, and the challenges of maintaining romance in the public eye.
His journey from early theater relationships through Hollywood marriage and post-divorce dating demonstrates resilience and growth. Astin’s willingness to be vulnerable about his experiences, particularly regarding loneliness and the challenges of single life, shows emotional maturity and self-awareness.
The actor’s romantic history also highlights the unique pressures faced by entertainment industry professionals in maintaining long-term relationships. Geographic separation, demanding schedules, and public scrutiny have all played roles in shaping his romantic experiences.
Rachel Reilly, the fiery redhead who captured hearts on Big Brother, has built one of reality television’s most enduring love stories. The 40-year-old reality star and television personality has been happily married to fellow Big Brother contestant Brendon Villegas since 2012, proving that some showmances really do stand the test of time.
Their romance began in the most unlikely of places – inside the pressure-cooker environment of the Big Brother house during Season 12 in 2010. What started as a mutual attraction between two competitive reality stars has blossomed into a thriving marriage spanning over a decade, complete with two beautiful children and continued success in the entertainment industry. Rachel’s relationship status has remained consistently stable, making her one of the rare reality TV personalities whose on-screen romance translated into lasting real-world happiness.
The couple’s journey from housemates to husband and wife has been documented extensively, from their initial meeting to their televised wedding and growing family. Their story serves as inspiration for fans who often wonder whether reality TV relationships can survive beyond the cameras. Rachel and Brendon have not only survived but thrived, building a life together that includes successful careers, parenting two young children, and maintaining their status as beloved figures in the reality TV community. Their relationship represents the gold standard for Big Brother couples, demonstrating that genuine connections can indeed form even in the most artificial environments.
Rachel Reilly’s Current Relationship Status
Rachel Reilly and Brendon Villegas (Image via Getty)
Rachel Reilly is currently married to Brendon Villegas, her longtime partner whom she met during Big Brother Season 12 in 2010. The couple has been together for over 14 years, having dated for approximately one year before getting engaged on Valentine’s Day 2011. Their relationship has remained strong throughout their time in the public eye, with both partners frequently sharing glimpses of their family life on social media.
The reality TV power couple tied the knot on September 8, 2012, in a lavish ceremony that was planned by celebrity wedding planner David Tutera and aired as a special on WE Network. Their wedding took place at sunset in Los Angeles and was attended by approximately 120 friends and family members, followed by a honeymoon in Aruba.
Meeting Brendon Villegas: A Big Brother Love Story
Rachel and Brendon’s love story began in the Big Brother house during Season 12, where their initial interactions were marked by skepticism and unexpected attraction. Rachel initially dismissed Brendon, telling E! News, “Brendon told us he was a swim coach and I said, I’m never going to fall for this guy. He’s just some swim coach.”
Brendon shared similar reservations, recalling, “Admittedly, I still remember that first night. Rachel was giggly and schoolgirlish about me, but I was very skeptical. Even though I liked her and thought she was cool, I was still very scared to fall for someone inside this game.” Their relationship solidified when they were both nominated for eviction, with Brendon noting, “When we were put on the block, that’s what cemented it.”
Despite Rachel finishing in ninth place and Brendon in sixth during Season 12, their connection proved stronger than the game itself. They returned together for Big Brother Season 13, where Rachel emerged as the winner, taking home the $500,000 grand prize.
Marriage and Family Life
Rachel Reilly and Brendon Villegas (Image via Getty)
The couple’s relationship moved quickly after leaving the Big Brother house, with Brendon proposing on Valentine’s Day 2011, less than a year after they first met. Their September 2012 wedding was a major television event, showcasing their continued popularity with reality TV audiences.
Rachel and Brendon have built a beautiful family together, welcoming two children who have become central to their lives. Their daughter, Adora Borealis Villegas, was born on April 8, 2016, after Rachel announced her pregnancy in September 2015. The couple expanded their family with the birth of their son, Adler Mateo Villegas, on November 11, 2020, following a pregnancy announcement in May 2020.
The unique names of their children reflect the couple’s thoughtful approach to parenting. Rachel explained their naming process: “Brendon is Latin, so we wanted kind of a Spanish name, and then we wanted something that would be unique and fun. And so I was just like, ‘What about Adora? I don’t think that’s a really popular name.’ And of course, she’s so adorable and we adore her, so it just made sense.” For their son, she noted, “And then with Adler, we wanted his name to be similar to Adora’s name. We wanted the names to both start with A, and then I found the name Adler and it means eagle. And I thought it sounded like a cool name.”
Professional Collaborations and Continued Success
Beyond their personal relationship, Rachel and Brendon have maintained successful professional partnerships. They competed together on The Amazing Race twice, placing third in both Season 20 (2012) and Season 24 All-Stars (2014). Rachel also participated in Season 31 with her sister Elissa Slater, finishing in seventh place.
The couple has leveraged their reality TV fame into various entertainment ventures. Rachel has maintained a recurring role on CBS’s The Bold and the Beautiful since 2010 and has worked as a reality TV correspondent for Hollywood Today Live on FOX. In 2022, they launched their own show, “Better with the Brenchels,” where Rachel serves as both host and executive producer.
Relationship Longevity in Reality TV
Rachel Reilly (Image via Getty)
Rachel and Brendon’s relationship stands out in reality TV, where showmances rarely survive beyond filming. Their marriage has lasted over 12 years, making them one of the most successful Big Brother couples in the show’s history. They’ve maintained their relationship through various challenges, including multiple reality show competitions, career changes, and the pressures of raising two young children in the public eye.
Rachel has spoken about how motherhood has changed her competitive nature, telling Yahoo! Life, “I’m really competitive on television, obviously, but when it comes to mom life, I don’t find myself to be as competitive. I’m not competitive with other moms at all. And my husband and I just kind of work together as a team.”
Their relationship continues to thrive as they balance their entertainment careers with family life, proving that their Big Brother romance was built on a foundation strong enough to last well beyond their reality TV origins.
