Single and Happy

19+ things to do when you're loving the single life in Fairfield County.

Photographs: ┬ędennisvdw/istockphoto

We’ve all been there — that moment when someone inevitably inquires about our relationship status.

“Are you dating anyone?” or “Do you have a boyfriend/girlfriend?” can sometimes feel like the most commonly asked questions. When the response is, “No, I’m single” we can almost cue the sympathetic facial expression followed by, “Don’t worry, you’ll find the right person eventually.”

But what if you weren’t worried? What if — gasp — you actually enjoy being single?

Contrary to popular belief, many people who are single are not desperately searching for Mr. or Mrs. Right. While they might eventually wind up in a relationship if the right person comes along, they can also appreciate the advantages of singlehood.

Yes, many people out there are single AND happy — and here are just some of the reasons.


Relationships can teach us a lot about ourselves, but there is a certain kind of self-awareness that comes from being single. Whether you recently went through a breakup and are navigating through life on your own for a change — or whether you can’t even remember the last time you were committed to one other person — when you have time to focus on yourself you can ditch your comfort zone and figure out what you truly want. Especially if you’ve spent years in a relationship and are new at living life solo, this is the perfect time to try the things you had always been scared to try. The best part is that nobody can hold you back, nobody is getting in the way of your self-focus, and you can become your own best friend in the process! (And maybe develop some new hobbies that will stick with you whether you're single or not!)

Here are some local options for learning something new about yourself:

Classes and Workshops



  • We rounded up local non-profits that need help during the holidays, but the truth is that many of these could use volunteers year-round!
  • Westport is home to a major disaster relief non-profit, AmeriCares.
  • Walk to end Alzheimer's or find another walk that supports a cause you care about.
  • The local LGBT Center holds new volunteer orientation each month. 
  • Spend time helping at United Way in Stamford or Greenwich.

Broaden Your Horizons Through Dating Different People

Just because you're single, it doesn't mean you can't date. Sometimes, casually dating different people is a great way to open your mind to new possibilities. Not everyone you date has to be a potential prospect for your FOREVER. Rather, the people you date can be people you just like to have fun with! Best of all, every person you date has something to teach you. 

For example, you may go on a few dates with a guy who encourages you to try an ethnic cuisine you’d never thought of trying before. You might meet that girl who takes you skydiving on the second date. You might grab coffee with someone who introduces you to your next favorite author and so on. When we’re in serious relationships, we tend to do most things with our significant other, and even the most adventurous people can tend to stick with what they know.

Here are some fun date ideas where you can try something new while learning about someone new:


  • Which local bars are favorite destinations for others in your age group? We've got the scoop.

So, get out there and have some fun — and let us know if you've got additional suggestions for Fairfield County single life!