Am I Ready to Date Again? 10 Questions to Help You Decide

Going out there to date needs to be a conscious decision. But, before you make that decision, you need to ask yourself some questions as this will really determine the level of success you will have.

My Own Experience

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

Heck, NO!

My life was in 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 my 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, as well as learning who I was on my own. 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. I’m 60. My youngest is a senior in HS and busy with her life. And just like that, I woke up one morning, and said to myself, “It’s time, I’m ready to date.”

Being my usual enthusiastic self, I spent part of the day writing my profile (revising it many times) and looking through my photos. I called my BF’s husband (a pro) 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. So, I uploaded my information, and the following week, I had 5 dates. Yes, 5. My stomach churns just typing this. For all 5 dates, I reached out first, didn’t do a single phone call, and kept the messaging to 2 messages each. Then, I asked each man out to lunch.

As a side note, I’m not a magician. I probably wrote to 25 men and only 5 got back to me, so pretty normal odds.

As you can see, 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 those thoughts down (because who the heck knows why they didn’t get back to me) and moved on positively to those that did.

5 Dates in 7 Days

Nope, I don’t recommend this type of speed dating, but my enthusiasm and go-go attitude got me in this pickle. I was happy with how those dates developed. Especially because I learned a lot about myself. For instance, I could still have conversations with men and be somewhat charming. My dating skills were still there, just a bit rusty.

Date 1 was with a hedge fund guy. He was polite and we had a great time, but there was no chemistry. The outcome: he invited me several weeks later to a dinner affiliated with Shark Tank producers, and I met some interesting people. I happened to be one of two women in the room that night – good odds!

Date 2 was a drummer in a rock and roll band. OMG. So out of my wheelhouse but such fun!

Date 3 was a Podcaster. The conversation just rocked though the chemistry was nowhere to be found. He has a full studio and invited me to use it when he was not. Such a nice guy!

Date 4 was the entrepreneur type. We bonded over both having lived in Chicago, and it went on to 3 dates before it fizzled. (I was impressed that I could still get a second and third date – yay, me!) My confidence got such a boost.

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!!!

It Was Exhausting

Have you heard the saying, “Do as I say, not as I do”? My dating marathon had me 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.

The Last One

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 of the message he sent me:

“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.

Following my own advice, we never talked on the phone. We just met for lunch, and I really liked him. As we met, I stuck out my hand to shake his; when the date ended, he shook my hand. I thought, “Oh, no, he doesn’t like me.” But the rest is history, and a year later here we are – a solid couple. We have chemistry and love, and I have a best friend with whom I have a blast! And, it turns out our first date was on his birthday, so we celebrated two milestones – him and us.

So, Are You Ready?

Hopefully you are still awake by this point, so let me share the questions I think you should ask yourself before jumping into dating – whether it be online dating, matchmaking, speed dating, hiring an expensive one-on-one matchmaker, or whatever.

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?
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? (If you do, 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 sharing my story, 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 to find happiness with. 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.

And if you’re not ready, take some time to just get to know you better. Then answer the questions again. I’ve had people come back to me 3, 6, 11 months after an initial conversation, ready and eager to start dating. So, it’s never too late.

Let’s Have a Conversation:

What’s your most recent dating experience? Which type of dating have you tried? Has it worked for you? What do you look for in dating? Do you ever ask yourself, “Am I ready?”