Hey, I'm Dylan
PhD turned realtor, Boston transplant, volleyball player, early morning runner, and your unofficial guide to making Asheville home.
The Quick Version
- • PhD from UF → Post-doc at Harvard → Burned out → Real estate in Boston → Moved to Asheville 2019
- • Gay guy from North Central Florida who found home in the mountains
- • Volleyball player at Highland Brewing (Tuesday & Thursday nights)
- • 6am runner on the RAD greenway, cortado enthusiast
- • Love the college town vibes mixed with mountain culture
- • Here to help you find your spot in this weird, wonderful city
Want the full story? Keep reading below or let's grab coffee
The Winding Road to These Mountains
Move-in day - October 2019
October 2019. I'm driving a U-Haul down I-40, my entire Boston life packed in boxes behind me, Wesley (my Springer Spaniel) riding shotgun, and my now-ex-husband following in his car. We're moving to Asheville, a city I'd visited exactly three times. Looking back, that level of confidence (or delusion?) still surprises me. But sometimes you just know when something's right.
The backstory matters here. I spent my twenties deep in academia, chasing a PhD in clinical and translational nutrition science at UF. My research focused on dietary therapy for kids with intractable epilepsy. The kind of work where you're literally changing lives, but also the kind that swallows your entire identity. After defending my dissertation, I landed at Harvard working on public health research. Dream job, right? On paper, absolutely. In reality, I was burning out faster than a cheap candle.
Here's something I learned: two things can be true at once. I loved that research AND I needed something different. When a family member casually suggested real estate during a holiday dinner, I laughed. Me? Showing houses? But the seed was planted. Within six months, I had my license and was selling homes in Boston. First year in, I won rookie of the year. Turns out all those years analyzing data and solving complex problems translate pretty well to helping people navigate the biggest purchase of their lives.
From PhD research at Harvard to Asheville real estate - quite the pivot
Why Asheville Called My Name
Boston was killing me softly. Don't get me wrong, I loved the walkability, the food scene, the fact that being gay was about as remarkable as preferring oat milk in your latte. But the pace? The cost? The winters that seemed designed to test your will to live? After years of that grind, I needed mountains. I needed space. I needed to remember what fresh air felt like.
My husband and I made a spreadsheet (because PhD habits die hard) of potential cities. We wanted: mountains, seasons that didn't require therapy to survive, a real food scene, walkable neighborhoods, and a place where we could be ourselves without constant explanation. Asheville kept rising to the top. Three scouting trips later, we were loading that U-Haul.
Early morning drives on the Parkway - this is why we moved here
Plot twist: the marriage didn't survive the move. Sometimes geographic cures work, sometimes they just clarify what was already broken. By spring 2020 (perfect timing with a global pandemic, right?), I was single, in a new city, trying to build a real estate business while the world shut down. Wesley and I spent a lot of time on the RAD greenway that year, processing life at 6am with nobody around but the herons.
Wesley has been my constant companion through all the transitions
Finding My People (Spoiler: It's at Highland Brewing)
Here's what nobody tells you about moving to a small city in your thirties: making friends is weird. Everyone already has their crews, their routines, their Thursday night plans. For about a year, I was that guy who knew all the coffee shops intimately but couldn't tell you anyone's last name.
Then I discovered volleyball at Highland Brewing. Tuesday and Thursday nights, 8pm, sand courts behind the brewery. At first, I just showed up alone, hovering at the edge until someone needed an extra player. Now? These people are family. We play hard, drink local beer, debate whether Flour or All Day Darling has better post-game food (it's Flour, fight me), and yes, there's a very gay subset of us who've turned Thursday nights into an unofficial queer sports league.
The Thursday night volleyball crew - found family at Highland Brewing
This is how Asheville works. You find your thing, you show up consistently, and suddenly you're part of something. For me, it's volleyball and running. For others, it's the drum circle downtown (not my scene but respect), trivia at various breweries, or the surprisingly robust pickleball community. The key is showing up. Keep showing up.
Finding community through art and outdoor activities
The Real Estate Thing
People always ask why I left academia for real estate. The short answer? Sanity. The long answer? I realized I was still doing the same core work: helping people figure out complex problems and find solutions that actually fit their lives. In research, I helped families navigate medical complexity. In real estate, I help people navigate finding home in a complicated market.
Growing up gay in North Central Florida, I always felt that outsider's perspective - belonging was distorted at best, and the concept of "home" felt disconnected. I spent my whole academic journey in Florida - undergrad and grad school at UF, building my career in Gainesville's college town atmosphere. After my post-doc at Harvard took me to Boston, I discovered I loved the urban energy but missed the college town vibes. Asheville gives me both - it's smaller than Gainesville but has that same intellectual curiosity and creative energy. Now my job is literally helping connect people to this place, to find their spot, their neighborhood, their coffee shop, their people. When clients text me six months later about loving their neighborhood or finally feeling settled, that hits different.
Showing houses during peak COVID - masked, sanitized, and still helping people find home
Plus, let's be honest, the flexibility is incredible. I can structure my day around a 6am run at Bent Creek, work from Rowan Coffee in West Asheville, show houses in the afternoon, and still make volleyball by 8pm. Try doing that in academic research.
The flexibility of real estate - morning runs and car is my office
Life at 35: The Current Chapter
These days, life has found its rhythm. I wake up stupidly early (5:30am is sleeping in for me), grab Wesley, and hit the trails or greenway before the world wakes up. There's something about seeing the mountains emerge from morning fog that never gets old. Coffee is always a cortado, always from Summit Coffee truck if I'm near RAD, or Hi-Fi if I'm feeling fancy.
Daily cortado ritual - I've tried every coffee shop in town
I'm in a relationship now with someone who gets why I need to run 40 miles a week and doesn't judge my obsession with tracking every coffee shop in town. We live in East Asheville, in a neighborhood that feels like you're in the woods but you're actually 10 minutes from downtown. Wesley has a yard. We have neighbors who wave. It's suburban in the best way.
Supporting LGBTQ+ businesses with my partner - community matters
Work is good. Really good. I've found my niche helping people (especially LGBTQ+ folks) navigate Asheville's wild real estate market. The market here is bonkers, but that's where having someone who actually lives here, who knows which neighborhoods flood, which coffee shops have wifi that works, and where you can walk your dog at 10pm safely, makes a difference.
The Gay Thing (Because People Ask)
Living here as a gay man is refreshingly unremarkable. I wear my jewelry to showings. My boyfriend and I hold hands walking down Haywood Road. Our neighbors are a mix of gay couples, straight families, and everything in between. Nobody cares, and I mean that in the best possible way.
Sure, the dating pool is small (everyone's dated everyone or they met at Highland during volleyball), and we only have one real gay bar, but the whole city feels queer-friendly in a way that bigger cities often don't. It's integrated rather than segregated. You don't need a gayborhood when the whole city is pretty gay.
That said, if you're moving here single and hoping for a bustling gay scene like Atlanta or DC, adjust expectations. Gay life here is more about hiking groups, brewery hangouts, and yes, volleyball, than club nights and circuit parties. Which honestly? At 35? Perfect.
What Nobody Tells You About Moving Here
Let me save you some time and tell you what actually matters about Asheville, beyond the Instagram shots and tourist board copy.
The size is everything. Asheville is just big enough that you have options (plural coffee shops, plural grocery stores, actual restaurants beyond brewpubs), but small enough that you'll run into the same barista at Trader Joe's. Coming from Boston where anonymity was guaranteed, this took adjustment. Now I love that the Summit Coffee truck guy knows Wesley by name and that I can't go to Haywood Common without seeing someone from volleyball.
The gay thing is both better and worse than you'd expect. Better because it's completely integrated into regular life. There's no gay neighborhood because we're everywhere. My accountant is gay. My dentist is gay. The couple three houses down is gay. It's just... normal. Worse because if you're single and over 30, good luck. The dating pool is roughly the size of a hotel hot tub, and everyone's already soaked in it. But honestly? Most of us came here for the mountains, not the meat market.
Seasons will mess with you. I'm from Florida originally, so I thought I understood seasons. I did not. January and February here will test your commitment to mountain life. It's not the cold (though 28 degrees is cold, fight me), it's the grey. The endless, soul-crushing grey. But then March hits, everything explodes in blooms, and you forget winter ever happened. By October, when the leaves are showing off and the temperature is perfect running weather, you're ready to get Asheville's latitude and longitude tattooed on your forearm.
Yes, winter gets cold here - Florida boy learning about real seasons
Playing tour guide when family visits - Biltmore with dad, Roan Mountain with mom
You need a thing. This is crucial. Asheville doesn't just hand you a social life. You need a thing that forces regular interaction. Volleyball saved me. For others it's trivia nights, book clubs, running groups, pottery classes, whatever. Pick something, commit to showing up even when you don't feel like it, and within six months you'll have actual friends. Not acquaintances, not "we should get coffee sometime" people, but friends who text you when you miss a week.
The housing situation is bananas. I sell real estate here, so believe me when I say: what you think you can afford and what actually exists are two different conversations. But here's the secret: East Asheville is underrated, Candler is having a moment, and if you're willing to drive 15 minutes, your options triple. Also, flood zones are real. Helene proved that. I don't care how cute that creekside cottage is, check the flood maps.
A Tuesday in My Actual Life
5:15am. Wesley's nose is in my face. He doesn't care that it's dark or that normal humans are sleeping. We have a standing appointment with the sunrise, and he takes it seriously.
By 5:45, we're on the RAD greenway. In summer, there's already light creeping over the mountains. In winter, we're running by headlamp like we're training for some apocalyptic ultra-marathon. Either way, this is my church. Six miles along the French Broad, watching herons fish, nodding at the same five early morning runners who are as crazy as me.
7:15am. Summit Coffee truck is just opening. "Cortado for Dylan?" They don't even ask anymore. I sit on the same bench, Wesley judges everyone walking by, I check emails and pretend to be a functional adult. The mountains are doing that thing where the morning light makes them look like a Bob Ross painting. Every damn morning I think "I can't believe I live here," and every damn morning I mean it.
8:30am. Team meeting at the real estate office. We talk market trends (spoiler: still crazy), share listings, gossip about which local restaurant is closing/opening/changing concepts again. I'm wearing nice jeans, a button-down, and yes, my jewelry. Nobody cares. This is Asheville.
10am-2pm. Showing houses to a couple from Charlotte. They want West Asheville walkability at Candler prices with mountain views and no flood risk. I gently adjust expectations while driving them around, pointing out coffee shops (essential), dog parks (critical), and which neighborhoods have the best trick-or-treating (surprisingly important to grown adults without kids).
3pm. Rowan Coffee in West Asheville, cranking through contracts and emails. The wifi actually works, the playlist is appropriately indie without being aggressive about it, and I can watch Haywood Road's parade of dogs and humans. This is my office most afternoons.
6pm. Home to grab a quick dinner (let's be honest, it's usually takeout from Sunny Point or a Trader Joe's salad), change clothes, argue with Wesley about whether he needs another walk (he always wins).
8pm. Highland Brewing, volleyball courts. Tuesday night is slightly less gay than Thursday but significantly more competitive. We play until we can't see the ball, then sit in the brewery arguing about whether that last serve was in or out, planning weekend hikes, gossiping about who's dating who now. Someone always knows someone who just moved here and needs friends. We adopt them immediately.
Post-volleyball hangs - this is how you build community in Asheville
11pm. Home, exhausted, sandy, happy. Wesley gets his final yard patrol. I scroll through Zillow looking at properties I'll show tomorrow, check the weather for Wednesday's run (will I need a headlamp AND rain jacket?), set my 5:15am alarm.
The simple pleasures - Haywood Road is the heart of it all
This is the rhythm. It's not glamorous. It's not Instagram-worthy most days. But it's mine, and it works, and I built it from scratch in a city that let me be exactly who I am. That's the real magic of Asheville. Not the mountains (though they help), not the food scene (though it's incredible), but the space to create a life that actually fits.
Why I Built This Whole Thing
Real talk? I got tired of having the same conversation 47 times a week. Every LGBTQ+ person considering Asheville asks the same questions: Is it really gay-friendly? Where do gay people actually live? Can I afford it? Will I find my people? What's the dating scene like? (Answers: Yes, everywhere, probably not what you're hoping but we'll figure it out, yes if you show up, and... well, it's complicated.)
When I was researching Asheville from Boston, the internet failed me. Everything was either "Asheville is a magical fairy wonderland of acceptance and craft beer!" (tourism board) or "Asheville is ruined, don't move here, we're full" (bitter locals on Reddit). Nobody was talking about the actual logistics of building a life here. Nobody mentioned that West Asheville floods. Nobody explained that "walkable" here means something very different than walkable in actual cities. Nobody warned me that dating in a small gay community means your ex will definitely be at the same brewery/coffee shop/volleyball game.
So I built what I needed when I was moving here. Real numbers about what things cost. Honest neighborhood breakdowns including which ones flood (looking at you, Biltmore Village). Actual places where gay people hang out (spoiler: it's mostly just regular places because we're everywhere). The truth about building community in a small city where everyone already knows everyone.
But here's the deeper thing. Growing up, my family moved constantly. Military dad, corporate relocations, always the new kid. I went to three high schools. Never had a hometown, never had that deep sense of place that some people take for granted. I think that rootlessness is why I'm so obsessed with helping other people find their spot. When someone texts me six months after closing, gushing about their neighborhood or the coffee shop they discovered or the friends they've made, that fills something in me that academia never could.
This site is also a love letter to Asheville, complicated as that love might be. This city gave me space to rebuild my life after divorce, to find real community at 30-something, to wake up every morning and choose joy (in the form of mountain views and excellent coffee). It's not perfect. The housing crisis is real. The infrastructure wasn't built for this many people. The recovery from Helene is ongoing. But it's home in a way nowhere else has ever been.
If you're reading this, you're probably in research mode. Maybe you visited once and felt something. Maybe you're burnt out on city life. Maybe you're gay and tired of explaining yourself. Maybe you just want mountains and decent coffee and a place where your dog can be happy. Whatever brought you here, know this: Asheville is absolutely worth it if you come with realistic expectations and a willingness to work for community. It won't just happen. You have to build it. But once you do? Magic.
When you're ready to stop researching and start looking at actual homes, reach out. I'll show you the neighborhoods, introduce you to my coffee spots, probably drag you to volleyball, and help you figure out if this weird little mountain city could be your place too. Fair warning: I'll probably have Wesley with me, and he'll judge your treat-giving inadequacies.
Here's What I Actually Do
I'm a realtor, yes, but that's just the technical title. What I actually do is help people (especially LGBTQ+ folks) navigate the wild process of finding home in Asheville. That means:
- Showing you neighborhoods at different times of day (because Saturday afternoon and Tuesday morning are very different vibes)
- Being honest about what your budget actually gets you (and creative about making it work)
- Introducing you to my coffee spots, my volleyball crew, my running routes
- Texting you when something perfect hits the market at 9pm
- Making sure you know which streets flood, which neighborhoods have water pressure issues, and where you can walk your dog at night
- Being the gay friend who already lives here and knows things
I don't do hard sells. I don't pretend every house is perfect. I won't tell you Asheville is right for you if it isn't. But if it is? I'll make sure you find your spot.
Let's Actually Talk
Whether you're seriously looking, just curious, or somewhere in between, I'm happy to chat. Coffee's on me (cortado for me, whatever you want). Wesley might join if it's a weekend.
Or just email me directly: dylanjlennon@gmail.com
Quick Facts for the Skimmers
I write about the real experience of living in Asheville - from neighborhood guides to dating disasters to why everyone here owns a Subaru.