Meet Dan Orlovsky!! - Westport Moms

How old are your kids and how long have you lived in Westport? My wife Tiff and I have 4 kids -Triplet 11 year old boys, Madden, Hunter and Noah, and a 7 year old daughter named Lennon. We have lived in Westport for almost 4 years now. I’m from Shelton so it’s not far from home, and Tiff is from Philly so It is very close to friends and family for both of us.

How did you end up where you are now in terms of your job? What do you like most about what you do? Feel free to share any details of how you ended up where you are (us moms LOVE a good story!) I ended up at ESPN because I started playing football at about 9 years old. As a kid I was obsessed with sports. I loved playing them, I loved competing, I loved trying to be the best. I ended up not sucking at football and played in High School at Shelton.

From there I went on a scholarship to UCONN to play football. I was very fortunate in that time to be around some great people who helped me learn accountability, work ethic, commitment, drive, leadership, and a ton of other important characteristics. I got drafted into the NFL when done playing at UCONN to the Detroit Lions. I went on to play in the NFL for 13 years for the Lions, Texans, Colts, Bucs, Lions and Rams. We moved a lot but we always stuck together.

I met my wife in 2006 at a wedding, and true story – I walked into the reception, saw her, turned to my friend behind me and said “I’m gonna marry her.”  Three years later, we were married. She’s always been my best friend since then, and the best wife and mother I could have ever prayed for. Moving around was amazing and hard…hard to make friends, hard to establish a home base, hard to raise a family. Once I got done playing in 2017, we settled in Philly thinking it would be forever. I started to break down football on social media because I’m a nerd at heart and I always thought people would be interested in it. It took off overnight and I was blessed to have multiple networks offer me roles on TV. I chose ESPN because I’m a CT kid at heart and ESPN was always the Mecca. I’ve worked just as hard in this 2nd career as I did my first, and I feel very blessed to be able to be doing what I’m doing.

What I like most about what I do is I get to be genuinely me. I love energy, I love pressure, I love attention. I love being the hardest working person in the room.

If you were not doing what you are today, what do you think you might be doing? If I wasn’t doing this, I would have likely chased a baseball dream of mine to be a professional baseball player. I never had a Plan B. I didn’t believe in one then and I still don’t. If plan A doesn’t work, find a new plan A was always my mindset – and still is.

What was your most memorable family vacation and why?  My favorite family vacation is the beach at sunset with my crew. Ordering pizza to the beach, watching the sunset, listening to country music and just being present. We go to Sea Isle City in NJ every summer and that’s my favorite place to be with my favorite people. I adore my wife and kids and being with them in that moment, and that will forever be my favorite place.

What is your proudest dad moment? My proudest dad moment constantly changes. I was proud when they were born, I was proud when they walked, I was proud when they talked. Right now our boys are in 5th grade and our daughter is in 2nd and they are full speed ahead with sports, and probably what I’m most proud about right now is that they are great kids. They’ve got great hearts, they know and love Jesus, and they love and respect and appreciate their mom.

What’s your workout of choice? Workout wise, I’m a maniac. Most of my workouts are based upon “pushing myself to feeling like I’m gonna quit and then not”. This means usually the Peloton or a Hiit workout. My wife and I work out a ton together, and usually everyday. We’re friends with Timmy Leary in town and Timmy always sets up these workout challenges that raise money for charity that really force us to stay committed to a goal.

What’s your favorite sport to play and/or watch (who do you root for?) My favorite sport is whatever one of my kids are playing. I loved football and baseball as a kid but now my favorite sport to play is golf. I play a ton at plenty of courses around here and a bunch at Longshore. My favorite teams are what my kids play on or for, including:
Westport Lacrosse
Westport Soccer
Westport Football
Westport Baseball
Eclipse Lacrosse Club

What’s your favorite restaurant in town? My favorite restaurants in town are Spotted Horse, Little Barn, and Viva’s!

What is one thing people would be surprised to know about you? One thing surprising about me is…well, there are two. First, I hate the dark. And am absolutely terrified of It. I don’t walk around my house when it’s dark; the lights are always on, and I don’t do scary movies! Two, I’m a movie crier…

If you had 24 hours to do whatever you wanted – what would you do? If I had 24 hours to do whatever I wanted, I would fly to Europe and play golf at Royal County Down!

What’s your drink of choice? I’m a red wine snob. Larkmead or Silver Oak are my favorites, along with Hall.

What is the one thing your spouse does that you are eternally grateful for? =) Tiffany always brings out the best in me. I can’t put into words what that has meant and/or done for me over the 14 amazing years we’ve been together. She’s an absolute rockstar.

What do you wish you could tell your younger self about being a father? Every moment is worth it. The ups, the downs, the easy, and the hard. It’s better than anything you’ll ever accomplish on a football field.

Scotch or Beer? 
Golf or Beach day? Beach with my family
Play sports or watch sports? Play
College football or NFL? NFL
Beer pong or ping pong? Ping
Hot wings or Mild Wings? Mild
Comedy or Drama? Comedy
Motorcycle or Mountain Bike? Mountain bike

Join The Westport Moms Community

Stay up-to-date with what is happening in-and-around The Westport, CT community with local events, community highlights, and exclusive deals.