Roy Briley, a real estate and insurance company owner, celebrated his 70th birthday on June 6, 2025, a day made extra special by the birth of his son, Roy Briley III. His wife, Glenda, 35, delivered the baby, who is now seven months old.
The couple, who share a 35-year age difference, first met in November 2020. At that time, Glenda had sought out Roy for advice at his workplace on establishing her own insurance business. She was 29.
Glenda immediately felt their “conversation flowed,” noting that despite their age difference, they share “more similarities than differences.” She described Roy as a “very driven individual, very hardworking, very successful,” which is how they connected.
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Glenda was drawn to their mutual attraction and appreciated Roy’s confidence in asking her to dinner, stating, “A lot of guys see a pretty girl and go shy.”
They hit it off immediately, leading Roy to invite Glenda to dinner that same night. They had a “wonderful conversation” and ended up going on four more dates within the next week.
Roy and Glenda quickly moved in together two months after meeting. Roy proposed on Valentine’s Day 2022 at the Captain Cook Hotel in Anchorage, and they had a small wedding with 20 guests on July 27, 2022.
Wanting a family, they began In Vitro Fertilization (IVF) in September 2022. Due to Roy’s past prostate cancer, sperm extraction surgery was necessary. Glenda also underwent an embryo transfer in December 2022.
After experiencing two miscarriages, on their third attempt, she successfully conceived their son in December 2024. Baby Roy Briley III was born on June 6, 2025, becoming Roy’s ninth child, joining the eight from two previous marriages.
Glenda told the Mirror, “It’s definitely given us something we’ve really looked forward to.”
She added, “With Roy being semi-retired and his other kids living their lives, this gives us something to do. All he does is hang out with his son. We plan life around him – it’s a busy life, and we definitely enjoy it, that’s for sure.”
Meanwhile, Roy, a semi-retired businessman living in Anchorage, Alaska, is committed to maintaining a healthy lifestyle for his wife and young son. This includes exercising on a treadmill six times a week, attending three to four gym sessions weekly, and strictly drinking only water since 2022.
He remarked, “I always feel from my perspective from people online thinking it’s not a good idea, I agree,” acknowledging the online criticism he receives.
“It just happens to work for us. I’m not the type of person to say things online, but for whatever reason, it’s worked out. From my perspective, too, I shot my best shot when I saw a beautiful woman. Roy has my wife’s face, and I couldn’t dream for anything better. When she smiles, her whole face lights up.
“I do feel as an older man a responsibility towards her and the baby to live the healthiest and best life I can. I’m certainly not perfect; I have never drunk in my lifetime and never done drugs. At this point in time, I’m healthy enough. I may not like 35 or 45, but I feel healthy and go on the treadmill six times per week.”
When discussing their family situation, Glenda admitted that it took time for relatives to accept the relationship. For instance, her 56-year-old mother, Rose, initially questioned if she was “sure” about dating Roy.
Roy, however, noted that while each family member reacted to their relationship “differently,” after five years, people are beginning to view them “pretty seriously.”
The couple regularly shares updates about their relationship on social media, including the anticipation of their son Roy’s birth, and they’ve observed a variety of reactions from online commenters.
Glenda noted that, overall, “A lot of people are very positive.” However, some comments question the age difference, asking things like, “Oh my god, how long is he [Roy Sr] going to live?”
“We’ve had some negative comments where people say really mean stuff like ‘oh my god, she’s there for the money. I really just ignore those type of comments. We have all these text messages from people saying ‘you inspire me and have given me hope, me and my boyfriends have an age gap and are trying to have kids.'”
The couple plans to have another child and is scheduled to begin their subsequent IVF cycle in December 2026.
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