Confession: I’m 32 years old, single, and haven’t been on a date in three years. Back then, I tried the online-dating thing ( Met some nice guys, went on several first dates, dated one good guy for a couple months. But I really hated online dating. It was a second job that took a lot of work, paid nothing, and wasn’t fun. As a woman, I had to double-check each guy’s story to confirm he was 1) telling the truth and 2) wasn’t psychotic, all while trying not to Google him too much and be a stalker myself. I didn’t rule out online dating as a “never again”, but I took a break from it… and haven’t been interested in going back.

It’s my own fault that I haven’t dated since then; I haven’t made the effort. I’ve been content, living my good life with plenty of work and hobbies and responsibilities to keep me occupied. And I like my independence. My self-sufficiency. The fact that I can do whatever I want, whenever I want, and don’t have to compare schedules with any other human being.

But the truth is, I’ve fallen into my comfortable routine, have gotten out of practice, and I’ve shied away from potential dates. I’ve let my introverted comfort zone take over (the lure of reading a good book in my favorite chair with my dog becomes ever more difficult to resist), and the more time passes, the harder it is to break out of it.

So part of this project is about exercising: exercising the skills and courage it takes to talk to an attractive, eligible member of the opposite sex and keep the conversation going. To keep that door open instead of shutting it after pleasantries.

Those skills are transferable—in a broader sense, I need to become more comfortable with talking to strangers, period. Men, women, old, young, married 50 years, or single and looking. I believe that by becoming more comfortable with all these people, and by forcing myself to get out of my comfort zone, the possibilities in my dating life will open up, too.

Activity Ideas: A Growing List of Fun Things I Want to Do

Inspiration: the Light-Bulb Moment