Kriti Mehrotra
After Pfeifer Hill spent an entire year working on herself, she decided to join the cast of Netflix’s ‘Age of Attraction’ in the hopes of finally meeting the person of her dreams. However, she knew she likely wouldn’t be interested in a man her age since they are “like a desk you have to assemble,” and she is completely done getting involved with furniture projects. Derrick Fleming was thus exactly what she was looking for, so they went on to get to know one another on a much deeper personal level once he admitted he shared the sentiment.
Pfeifer Hill and Derrick Fleming Navigated Every Concern With Open Communication
The moment Pfeifer Hill and Derrick Fleming locked eyes at the beginning of their 3-minute speed date on the very first day, it was as if sparks erupted owing to their innate chemistry. They were both giddy to feel such an instantaneous connection, yet it only grew stronger over the ensuing few days as they realized they also shared similar beliefs, perspectives, and values. The former was waiting for the other shoe to drop throughout this period because she felt it might be too good to be true, or that their calm passion might burn out, but she was wrong.
Derrick later did tell Pfeifer that he was actually a father of 2 boys, but aside from changing how old she thought he realistically was, it didn’t alter her feelings toward him or anything else. So, they made their way to the Promise Room, where they validated each other even amid heightened emotions, then revealed their ages and decided to step into the real world hand in hand. Their 20-year age gap was significant, especially with her being 23 while he’s 43, yet it didn’t really cause issues for them as they were always communicative, honest, intentional, and understanding. Even when discussing her worries about how he might introduce her to his sons or the possibility of relocation if things panned out, they were on the same page because they prioritized the same thing: family.
However, Pfeifer and Derrick’s seemingly idyllic bond hit a bit of a snag when it came time for them to be introduced to one another’s loved ones, as the former grew incredibly nervous. She admittedly began overthinking everything, yet it ultimately came to light that she had nothing to worry about since both her parents and his cousin could see how great they were together. They understandably had some concerns owing to the couple’s 20-year age difference as well as the fact that his children would soon be involved, but they also couldn’t deny the care, joy, and spark they could see. Yet things changed when Pfeifer thought about what’s next, realizing she would be giving up a lot to move from Seattle to Dallas for him, and she had promised herself she would never change for a man.
Pfeifer Hill and Derrick Fleming Have Parted Ways on Amicable Terms
Although many from the outside looking in may have assumed Pfeifer and Derrick were at entirely different stages in life due to their big, two-decade age difference, that couldn’t be further from the truth. They were ready to get into a serious relationship with the intention of making it last forever, while building a loving family, maintaining a calm home, and providing stability for their young ones. In fact, while she stated that their age difference as well as his being a father of two are “positive challenges,” he made it clear that he understood her concerns about moving and possibly losing herself in the process. Therefore, with her agreeing to move before vowing to care for not only him but also his sons, and he promising to ensure she never feels less like herself or lonely, they committed to one another.
The most beautiful moment between Pfeifer and Derrick was when he gave her a key to his home and said it was now theirs, because he could not bear the thought of her living anywhere else when she does relocate. He made it clear that they were together in this relationship as equal partners, no matter what, but alas, the couple couldn’t make things work between them upon returning to the real world. As per the father of two in the reunion special on ‘The Viall Files’ podcast, they parted ways on amicable terms after some of the questions that had come up during filming continued to linger. He asserted that although she isn’t at the reunion, there is no bad blood between them and that they still have a lot of respect for one another. Pfeifer later revealed on her social media that she skipped the reunion because it clashed with her birthday trip to Japan with her new boyfriend, and she wanted to focus on that.
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Pfeifer Hill is a Thriving Graphic Designer, Whereas Derrick Fleming is a Devoted Medical Salesperson
Pfeifer was reportedly quite young when she realized she had a passion for the creative world, driving her to enroll at the University of Washington as soon as she graduated from high school. She is currently pursuing a Bachelor’s degree in Design/Visual Communication Design and is all set to earn her credits by the summer of 2026, meaning she is scheduled to graduate then. However, it’s imperative to note that the fitness, self-growth, and wellness enthusiast had kick-started her career in 2022 itself, taking on the position of a Keyholder at SoulCycle Inc. She even held titles as a part-time receptionist, a Stanley Design Intern, and a University Illustrator before securing her first full-time job as a Brand Design Intern at EA Sports in June 2025. She serves in that role to this day in Seattle, Washington, all the while embracing her passion for travel as well as spending quality time with loved ones.
On the flip side, despite having a Bachelor’s degree in Political Science and Government/History from Lyon College (2004), former baseball athlete Derrick is now a Vaccines and Immunology Specialist. He kick-started his corporate career in the field of sales before joining ADP in 2009, where he worked as a Senior District Manager prior to getting promoted to Corporate Sales Trainer in 2010. The Dallas, Texas, resident worked there until 2014, all the while maintaining the title of Co-Chief Executive Officer at the Under the Lights Baseball Academy from 2011 to 2014. Then, he joined Medline Industries, where he held various positions over a period of over 12 years before jumping ship to spread his wings at Syneos Health in September 2021 as a Vaccines & Immunology Specialist. On a personal level, he is a father of two, but he also leads a very high-energy lifestyle, full of concerts, gym sessions, as well as travels alongside his loved ones. We should even mention that it appears as if he is currently focusing on earning his pilot’s license, too.
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