If you were scrolling through Instagram in late 2023, you probably saw a very silver-haired Patrick Dempsey grinning like a kid who just won the lottery. He’d just been named People’s Sexiest Man Alive. But while the internet was thirsting over "McDreamy" in his late fifties, a smaller group of fans was focused on the tall, sharp-featured teenagers standing next to him on the red carpet. Specifically, Sullivan Patrick Dempsey 2023 became a massive talking point because, frankly, the kid looks more like a young Hollywood leading man than his dad did at the same age.
Sullivan isn’t just "one of the twins." He’s the one who inherited the acting bug. While his twin brother, Darby, usually leans into sports and a more reserved vibe, Sullivan has spent the last year or so leaning into the spotlight.
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The Year Sullivan Patrick Dempsey 2023 Stepped Out
2023 was a pivot point for the whole Dempsey clan. Patrick was out promoting Ferrari and the slasher flick Thanksgiving, and for the first time in a while, the family wasn’t hiding from the paparazzi. At the Los Angeles premiere of Ferrari in December, the entire family showed up. Sullivan looked effortless in a suit, sporting a narrower face and those high cheekbones that he clearly got from his mom, Jillian Fink.
People always try to compare the twins. It’s unavoidable. But Sullivan Patrick Dempsey 2023 showed us a kid who is comfortable in his own skin. He’s got this "funny expression" thing his dad always talks about—a way of taking in a room that feels more like an observer than a participant.
Patrick has been pretty vocal about how hard it is raising teens in Hollywood. He told People back in November 2023 that it’s "harder" now than when they were little. Why? Because they want independence. They want their own identity. Sullivan is right in the thick of that. He’s 17. He’s navigating the shadow of a father who is literally a global sex symbol while trying to figure out if he actually wants to be on screen or just near it.
Personalities: Sullivan vs. Darby
The most interesting thing about Sullivan is how different he is from Darby. They’re fraternal, not identical, which Patrick says was obvious from day one. When they were born in February 2007, Darby had blond hair. Sullivan? He had what Patrick calls "Sid Vicious black, punk-rock hair."
By 2023, that hair has lightened up, but the personality remains distinct.
- Sullivan is the "funny" one.
- He’s the one interested in acting.
- He’s physically active but more focused on the creative side of things.
- He’s got a "silky mane" that resembles his mother's more than the classic Dempsey "thicket."
Growing Up in the Shadow of "McDreamy"
It can’t be easy. Imagine your dad being named the sexiest man on the planet when you’re a junior in high school. Sullivan and his siblings reportedly just make fun of him for it. That’s the vibe in the Dempsey house—they keep him humble.
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In 2023, Sullivan was largely finishing up his time at Crossroads School for Arts & Sciences in Santa Monica. It's a high-pressure environment, even without the famous last name. Patrick has mentioned that he tries to model good behavior rather than lecturing them. He wants Sullivan to make mistakes. He wants him to find his own boundaries.
Honestly, that’s probably why we don't see Sullivan in a Marvel movie yet. The parents are protective. Jillian is a massive makeup mogul, and Patrick is... well, he’s Patrick. They’ve built this "calm, loving, safe environment" that seems to have actually worked. Sullivan isn't a tabloid fixture. He’s just a kid who happens to have a very famous face.
What’s Next for Sullivan?
The "acting bug" is a real thing. Patrick has confirmed that Sullivan is the one who has shown a genuine interest in the craft. In 2023, that interest seemed to be maturing. While his older sister Talula is carving out a path in the culinary world (launching Talula’s Kitchen), Sullivan seems to be the heir apparent to the Dempsey screen legacy.
But there’s a nuance here. Sullivan isn't rushing it. He spent most of 2023 just being a student, attending events like the Monster Energy Supercross Celebrity Night, and staying active with his dad. They bike, they play tennis, they stay moving. Patrick’s philosophy is simple: if you sit too long, you lose it. Sullivan seems to have taken that to heart.
Key Takeaways for Fans of the Dempsey Family
If you’re following Sullivan’s journey, keep an eye on these specific traits and upcoming shifts:
- The Look: He’s moved away from the "punk rock" hair of his childhood into a more refined, editorial look that favors Jillian’s features.
- The Career: Unlike Darby, who is more sports-centric, Sullivan is the one to watch for future casting calls.
- The Education: Having graduated in early 2025, his 2023 was the "calm before the storm" of college and career decisions.
- The Humor: Every interview with Patrick mentions Sullivan’s wit. He’s likely the one writing the scripts or delivering the punchlines in the family group chat.
Sullivan Patrick Dempsey is at a crossroads. He has the name, the look, and the talent, but he also has a family that doesn't force the spotlight on him. Whether he chooses to pursue Hollywood or stay behind the scenes, his 2023 showed a young man who is more than just a famous son. He's an individual who's clearly ready for whatever "next chapter" he decides to write.
To get the most out of following Sullivan’s potential career, focus on his involvement in independent creative projects rather than looking for him in big-budget sequels just yet. Watch for his name in credits for short films or theater productions, where he’s likely to hone his craft away from the "McDreamy" label.
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Next Steps: You can check out Patrick Dempsey’s official Instagram to see the rare family photos from the Ferrari premiere to see the resemblance for yourself. Or, look into Jillian Dempsey’s product line, as she often shares behind-the-scenes snippets of the boys during family outings.