Reading: Am I Ready to Date Again?

After a 24-year marriage, I found myself divorced in 2018. And questioning: Am I ready to date? Heck, NO! 

Finding your way back into the dating game is not for the faint of heart. And this is coming from me… a dating coach! I founded It’s Just Lunch matchmaking service (years ago, after being dumped by my fiancée 5 weeks before the wedding, and where I met my now ex-husband) and, later, founded 33000Dates.com. 

Yet just a few years ago my life was in such transition — moving from the big house to a new condo, my daughters in their early teens — and I just couldn’t fathom adding dating to this confused tableau. The girls were the priority and they were at very formative years (and thinking about dating themselves). So imagine Mom dating, too? It just felt, well, not right. Stability was my focus and learning who I was, alone, was my goal.

When Is the Right Time to Start Dating Again?
Fast forward fives years. Youngest is a senior in high school and busy with her life. And just like that, I woke up one morning, and said, “It’s time, I’m ready to date.” That day I wrote my profile, called my best friend’s husband (a professional photographer) and asked him shoot a few new photos to mix with my iPhone and Instagram photos, and was off to the races.

I don’t mess around. I knew the two sites I wanted to begin with. Boom. I’m on. The following week I have five dates. Yes, five! (My stomach churns just typing this.)

With all five men, I reached out first, didn’t do a single phone call, and kept the messaging to two messages each. Then, I asked them out to lunch. I probably wrote to 25 men in total and only five got back to me — so, pretty normal odds. Five Dates. Seven Days. Nope, as a dating expert, I don’t recommend this, but my enthusiasm and go-go attitude got me in this pickle.

Okay, so the dates — all lovely. I learned so much. I could still have conversations and be somewhat charming. My dating skills were still there, just a bit rusty. 

Date 1: A hedge fund guy. Totally polite though we both knew no chemistry. The outcome: He invited me several weeks later to this dinner affiliated with Shark Tank producers and I met some interesting people.

Date 2: Drummer in a rock and roll band. OMG. So out of my wheelhouse but such fun.

Date 3: A podcaster. The conversation just rocked… the chemistry was nowhere to be found. But such a nice guy!

Date 4: Entrepreneur type. We bonded over both having lived in Chicago, went on three total dates before it fizzled.

Date 5: A doctor. Not a single thing in common so I just went quiet and listened to him talk about the latest advances in skin care and vitamin therapy. I learned quite a bit from him; it was like a free consultation!

Success? Not really. So do as I say, not as I do, as the saying goes. I was exhausted after that week.

But there was this one mystery man I hadn’t met or connected with yet. I was drawn to him because here was his message: “You know what impressed me most about you? That you host Thanksgiving yearly for family and friends and do all the cooking yourself for 40 people… Wow!” That melted my heart. He wasn’t impressed by anything I’d done business-wise, and instead he got to the heart of something I care tremendously about — family and friends.

We met for lunch, and boom: I really liked him. When I initially met him, I stuck out my hand to shake his — then the date ended and he shook my hand. I thought… Oh, he doesn’t like me. Not true. He was just being polite.

A year later, we are a solid couple, with chemistry and love between us. And he’s a best friend with whom I have a blast! And, it turns out, our first date was on his birthday so on that dating anniversary we celebrated two milestones — him and us.

Are You Ready to Date Again? 10 Questions to Ask
From my own personal experiences and my professional expertise, here are the 10 questions I think you should ask yourself before jumping into dating — whether online dating, matchmaking, speed dating, or hiring an expensive one-on-one matchmaker:

1. Am I feeling positive about dating?
2. Do I feel like I’ve moved on from my ex? Can I not talk about my ex on the date?
3. Do I feel excited and nervous at the same time to start dating again? (If yes, that’s the right answer.)
4. Am I in a good place professionally to have the time to devote to dating?
5. Am I realistic in what I am looking for?  
6. Do I have a list of 10, 20+ traits that are deal breakers for me? (Burn it.)
7. Am I happy with my own life?
8. Do I have friends and a good support system?
9. Am I active in my hobbies or sports or passions?
10. Do I have some confidence? (Not many people have 100% confidence going into dating! But it’s important to be self-aware and have healthy self-esteem.)

Andrea McGinty founded It’s Just Lunch dating service in 1991 (before online dating was a thing!) and is currently the founder of 33000Dates.com, which helps singles navigate online dating. She specializes as a dating coach for people in their 40s–70s and has helped 6,000+ couples to marriage. Andrea has been featured on Oprah, The Today Show, People, Forbes, The New York Times, and more.