Lessons from the Different Stages of Dating

As always, I like to bring my real dating experiences to you so we can all learn together from these relevant lessons. So, today’s article is about Bob (not his real name).

I connected with Bob on Match.com, which is where I meet most of the men I date. I really enjoy online dating and believe it’s a good fit for me.

Texting or Calling?

We chatted through the platform for a day or so and then exchanged phone numbers so we could connect more personally. Typically, I like to go from text to a phone call, and then to a date all within about seven days. It helps keep the fire blazing until we can meet and see if there is any real connection.

In Bob’s case, I discovered he didn’t like to talk on the phone much at all, so he was a texting fiend, and he was going out of town for work. Warning: if a man can’t meet you in person within 10 days, there is a high probability that he’s a scammer. I was a little concerned about that, but we had a date scheduled for later in the week, and I wouldn’t be out anything if he cancelled.

So, we texted for eight days, which is longer than I have ever texted a man in my entire dating experience. It wasn’t all bad because we had some in-depth conversations that we probably wouldn’t have had if we were talking face to face, but it still was weird. Texting is time consuming, and I’m not a huge fan but it’s not a deal breaker.

So We Finally Met

When I walked in, I was pleasantly surprised. He was better looking than his photos, dressed nicely, and wore grown up shoes. I know that sounds silly, but that’s important to me. I take time and effort to look nice on a first date, and I like my date to do so as well. I also knew that he was smart, funny, and knew how to adult without any mothering. All good things.

We had fun on our eight-hour date. There were no awkward silences and chemistry was brewing. However, you would have thought that with all that previous texting, I would have discovered that he was only five months past a live-in relationship. He didn’t tell me how recent his breakup was, and I was surprised and taken aback. I was his first date after the previous woman. Hmmmm…. But, in all fairness, I didn’t tell him I was a dating coach either, so I guess some things are better talked about in person.

During that very long conversation I learned that he never talks on the phone unless there is an emergency, has very quirky eating habits, and has a behavior disorder that causes him to be obsessively accurate and rigid in some of his beliefs. Another hmmmmm…

I didn’t see any of that on our first date at all, so I agreed to a second.

Second Date

Even on our second date, I didn’t see any red flags. What I did learn, however, was that he was scared to death of making another mistake in his love life and was absolutely not ready to move on romantically. I’m not sure he knows that yet, but I do.

No one can guarantee roses and fairy tales after a few dates. Even long-term relationships need consistent nurturing to maintain that ‘in love’ feeling. It was obvious that we are at different stages in our journey to finding love.

I like him a lot. He’s fun, funny, we have tons in common, and we can have deep conversations. Even so, I was fairly certain that we wouldn’t have a third date as a result of how he was feeling.

In the End

He sealed the deal the next day when he sent me a text that read, “Hope ur appts went well today. I don’t necessarily feel like talking much tonite (but can if you want).” Mehhhh, not really. I didn’t care one way or the other. If there was any doubt for me, this made it crystal clear that we’re not a love match. Both of us should have been excited to talk to each other by this time. And neither of us was.

His no phone communication style seems childish to me, and I can feel his closed heart. Overall, it didn’t feel good enough for me to want to invest any more time. So, I moved on easily with a text without any hard feelings.

All About Lessons

I learn something with everyone I meet. This is exciting because as I coach my clients, I tell them that every man they date brings them closer to the right man for them. And I feel like I’m seeing this for myself as well.

The last two men I dated have been closer to what I’m looking for in a partner than any other men I’ve met in the past. I can feel myself getting closer to the right guy. The key for all of us is to focus on having fun, remain true to yourself, and keep an open heart so you can catch cupid’s arrow when she sends the right one for you.

If you want to learn more about the four key ingredients you need to find love over 50, grab an autographed copy of my book, The Perfect Dating Guide for Women over 50. It helps smart, savvy women date with clarity and confidence so they can find the special someone who adds that little bit of spice into their life.

Let’s Have a Conversation:

Would you date someone who told you they had a compulsive personality disorder? And what boundaries would you set?