Ready to cuff: Tired of swiping, Sherwood singles bet on in-person matchmaking
“Dating should still involve actually meeting people,” says Epiphany Match co-founder
SHERWOOD, Ore. — With the autumn months beginning and holidays closing in, ‘tis the season for singles to pair up and settle down — also known as “cuffing season.”
Despite the prominence of dating apps, a local matchmaking boutique says they are seeing more people actively asking for ways to meet organically and in-person again.
Newberg-based concierge matchmaking firm Epiphany Match often holds speed dating events in Sherwood at 503 Uncorked wine bar.
Crystal Boles, co-founder of Epiphany Match, said the term cuffing season can be fun, after an unserious summer of travel, vacation, and outdoor time.
“As summer ends, we tend to see people shift from ‘I'll see what happens’ to being much more intentional about finding a relationship. Then, fall hits and … people become more intentional,” Boles said. “The weather changes, routines settle down, and suddenly having someone to spend those cozy weekends and upcoming holidays with starts sounding pretty appealing.”
Deciding if a date is serious enough to bring home for Thanksgiving and holiday parties to meet the family raises the stakes.
“In communities like Sherwood, people often tell us they want someone who fits into their actual life and community,” Boles said. “Geography matters more than people sometimes realize, particularly for busy professionals and parents. Creating opportunities for people to meet other singles closer to home can make dating feel much more manageable.”
She said the company is consistently hearing from single clients that they still want meaningful relationships, but are increasingly tired of dating apps.
“More than anything, people are telling us they want a real connection,” Boles said. “They’re looking for someone who is emotionally available, relationship-minded and actually willing to show up and date intentionally. There’s definitely less patience for endless texting, situationships and ambiguity.”
She said dating apps cause decision fatigue with endless profiles to swipe on, so people start treating dating like shopping — but then they see a lot of ghosting, outdated profiles, and have trouble knowing who is genuine.
That frustration is not unique to Oregon. In the 2025 Singles in America study from Match and the Kinsey Institute, 47% of singles surveyed said they felt burned out by dating, while 54% said the modern dating landscape left them drained.
“Chemistry is incredibly difficult to determine from a photograph and a few lines in a profile. They want events, introductions and opportunities where they can actually have a conversation and experience someone’s personality,” Boles said. “That desire for face-to-face connection is one of the reasons we’re creating more opportunities for singles to meet in person.”
According to Boles, intentional dating doesn’t mean every first date has to feel like a job interview, as long as you’re curious to learn more about the other person.
“It means knowing what matters to you, being honest about what you’re looking for and giving connections enough of a chance to develop,” Boles said. “As matchmakers, we often encourage people to look beyond the first date and pay attention to how they actually feel when they're with someone.”
She said her clients ask for emotional availability, communication, consistency, shared values, and lifestyle compatibility.
“Attraction still matters, of course, but we're hearing more people say they want someone who follows through, communicates clearly and is genuinely ready for a relationship,” Boles said. “We’re also noticing an interesting shift from a couple of years ago, when politics seemed to be much more front and center in dating conversations. Political compatibility can certainly still matter, but … it feels less about agreeing on every issue and more about whether two people can actually build the kind of life they both want.”
On September 27, Epiphany Match will be at Sherwood’s 503 Uncorked for a Singles Sunday Funday speed dating event, featuring three staggered, separate age-based speed dating sessions, from 2-6:15 p.m.
Tickets cost $30, and include one drink, a light snack, and a complimentary professional headshot photo. The sessions begin with a 15-minute mingle, followed by an hour of hosted speed dating facilitated by professional matchmakers.
“What we love about these events is watching the energy change once people actually start talking to one another. People can arrive nervous or unsure about speed dating, but once the conversations begin, they remember that meeting someone in person can actually be fun,” Boles said. “We thought the headshot would be a fun addition because even as we're encouraging people to get off their phones and meet face-to-face, we know many singles are still using dating apps. So even if someone doesn't meet their person that afternoon, they leave with a great professional photo they can use in their dating profile.”
Boles said people tend to give weight to instant chemistry, which can be a great way to find a partner, but doesn’t necessarily indicate healthy, long-term compatibility.
“We also wish people would slow down and actually learn how to have a conversation with each other,” Boles said. “A great date shouldn't be one person interviewing the other, but there should be genuine back-and-forth. Ask questions. Listen to the answers. Be curious. Give someone enough time to show you who they are. Sometimes, the person who doesn't create fireworks in the first five minutes is the person you discover you can actually build something meaningful with.”
Singles Sunday Funday Speed Dating
Where: 503 Uncorked
Web: 503uncorked.com/4/
When: September 27
Cost: $30
Ages 50+: 2:00–3:15 p.m.
Ages 35–50: 3:30–4:45 p.m.
Ages 21–35: 5:00–6:15 p.m.
Jules Rogers
