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Am I ready to date again? 10 Questions

Yes, it’s a decision. But I’d ask myself some questions first as this will really determine the level of success you will have.

I’ll give a personal example. After a 24-year marriage, I was divorced in 2018. Was I ready to date?

Heck, NO!

(And you all know what I do professionally…from the founding of It’s Just Lunch Matchmaking Service in 1991 where I met my now ex-husband, to selling the company at its peak---to doing what I love again as a dating coach and having one on one contact with clients and having set up over 33,000 dates in my life thus far!).

My life was in such transition---moving from the big house to a new condo, my daughters in their early teens---I just couldn’t fathom adding dating to this confused tableau. The girls were the priority and they were at very formative years—imagine throwing in a mom dating a slew of men to the picture? It just felt, well, not right. Stability was my goal and learning who I was alone. Plus, I knew the West Coast was probably not my permanent home any longer with the girls growing up and heading to the East Coast.

Fast forward 5 years. Youngest a senior in HS and busy with her life. And just like that, I woke up one morning, had an aha moment

and said “It’s time, I’m ready to date”. For those of you I am fortunate to work with, you know me, and I jump enthusiastically into things. That day I wrote my profile (no, I still don’t recommend you all writing your own!!!), went with the first draft (for you all, I generally am a bit nuts and revise 4 times minimum before sharing with you), looked through my photos, called my BF’s husband (a professional photographer) and asked him for an hour to shoot a few new photos to mix with my iPhone and Instagram photos and was off to the races in one week.

I don’t mess around. I knew the two sites I wanted to begin with. Boom. I’m on. The following week---I have 5 dates. Yes, 5. My stomach churns just typing this. All 5 men I reached out to first, I didn’t do a single phone call and kept the messaging to 2 messages each---then asked them out to lunch. (Yes, of course, I’m not a magician---I probably wrote to 25 men and only 5 got back to me—so pretty normal odds). But, yeah, I went through all the stuff you go through---there were a couple of very cute, accomplished men---that never responded back and I wondered why. But I quickly shut down those thoughts (because who the heck knows why they didn’t get back to me) and moved on positively to those that had.

5 Dates. 7 Days. Nope, I don’t recommend this but my enthusiasm and go-go attitude got me in this pickle. Ok, the dates---some lovely, but all just fine and in the ballpark. 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. Oh, I was one of two women in the room that night—good odds! Date 2: A drummer in a well-known rock and roll band. OMG. So out of my wheelhouse but such fun. Date 3: a Podcaster. The conversation just rocked---but the chemistry was no where to be found. I kept thinking of girlfriends I'd fix him up with---maybe even my sister Joanna. He has a full podcast and broadcast studio and invited me to use it when he was not. Such a nice guy! Date 4: Entrepreneur type. We bonded over both having lived in Chicago---and it went on to 3 dates before it fizzled. (Wow, I can still get a second and third date---yay, me!). My confidence blooms. Date 5: a doctor. Oh, 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!!!

“So do as I say, not as I do.” I was exhausted after that week, plus I couldn’t remember what I talked about with each person. And you don’t want to look flakey on a second date repeating a story over again, right?

I took a break---for me, that meant two weeks to see how a few second dates would go.

But there was still this one mystery man I hadn’t met. He lives in South Florida near me, but he’d messaged me he was up at the Cape for a few weeks. 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---he got to the heart of something I care tremendously about---family and friends.

No, we never talked on the phone. We just 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, no, he doesn’t like me. (I've lived this too, my dear clients and friends---and I get it, I really get it!) But the rest is history, and a year later here I sit, a solid couple, chemistry, love, a best friend with whom I have a blast! And, it turns out our first date was on his birthday so July 21 we celebrated two milestones---him and us.

Hopefully you are still awake; here are the questions I think you should ask yourself before jumping into dating—whether online dating, matchmaking, speed dating, 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 dealbreakers 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!).

Well, I got a bit personal but my business of helping singles navigate online dating is super personal to me and my heart. I like people to be happy. I love when you find a partner and love. I’m thrilled if you are widowed and meet someone you truly like. I’m excited when you haven’t dated in a few years and you call or text me late on a Saturday night with happy news.

You can talk to me for 15-minutes on the phone for free. By the end, I’m straightforward as I can only take a certain number of clients each month. If I think you are not ready, I will tell you and also why. Yes, people come back to me 3,6, 11 months later ready and eager. But it’s worth a chat if you’d like to find love…or just date again. Either works for me!


Andrea McGinty

Dating Coach, Relationship Strategist and Online Dating Counselor

Founder, Founder 702-494-7344 (I live on the East Coast)

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