Dating in the Life of a Dating Coach over 60

One of the benefits my coaching clients get when working with me is that I’m walking the walk and talking the talk right along with them. I’m single, over 60, and looking for love. Because of this, I thought it could be helpful for you to go on a first date with me to see how I handled some of the unexpected things that can come up and learn the thinking behind my decisions.

There are so many little things that come up on a first date that factor into the question of “Do I like him or not?” Those are the things that can cause anxiety because you don’t know how to handle them. I hope this gives a little more insight.

Until I find my someone special, I try to keep three men in a dating rotation. I meet 99% of the men I date online. And in most cases, I talk with them on the phone first. I don’t date every man I talk to. If I don’t feel as if we’ll at least have an interesting conversation, I pass.

Dismantling My Date with Bill

Bill (not his real name) was a couple of years younger than me and not Brad Pitt, but attractive. When we chatted on the phone, the conversation was good, and we had some fun things in common. There was enough chemistry that I agreed to meet for coffee. I like coffee dates because they are simple and help avoid any anxiety about who pays. I like a man to woo me and pay on the first date. Coffee dates make that easy. 

This time my coffee date turned into dinner instead, but it was still simple. I asked Bill to pick the location, again because I enjoy masculine energy. He selected a restaurant that was nice for a casual dinner and not upscale or too pricey for my comfort level.

Bill Was Pleasant at Dinner

We laughed and had a great conversation. He was polite, respectful, funny, and friendly to the waitstaff. Even though he told dad jokes, they were cute until their humor began to fade as the evening wore on. I think he may have been nervous, so I allowed for that.

Because I’m a dating coach and a certified hypnotherapist, I like to talk about my job in person rather than over the phone. I like to see my date’s reaction to help me gauge his level of self-confidence. Men who lack confidence tend to be intimidated by what I do for a living, and I like to know that before things go too far.

I keep date number one easy-breezy. This is the time to simply determine if I like his company enough to want to get to know him even more. Bill was fine with my job and thought it was interesting.

As the evening progressed, I discovered that the reason we met for dinner was that he had a coupon for the restaurant. Hmmmm, I’m not opposed to saving money, but a girl does like to feel like she’s worth full price. If it were me, I probably wouldn’t have said anything about the coupon and thought that was a little tacky.

There was innocent flirting during dinner. He touched my back to guide me to and from our seat, which I liked. And as we walked out of the restaurant, he grabbed my hand which was nice.

Then He Asked Me If I Wanted to See Him Again

I’m a big believer in the 3-Date Rule. If my date is nice, fun, and respectful on our first date, even if I don’t feel any crackling chemistry, I will give it two more dates to develop. If, after three dates I still don’t feel any chemistry, there probably never will be any and that’s when I move on.

When I said, “Yes, I’d like to see you,” things got weird. This is when he felt the need to double check my decision by badgering me with, “Really, you really want to see me again, you’ll really see me again, you’ll actually see me again.” Finally, I said, “If you keep asking me that, I’ll probably say ‘No’.”

I was teasing, somewhat, but his response caught my breath. He told me to “Shut up.” I believe his comment was simply a knee-jerk reaction, but it still immediately made me wonder what an argument with him would sound like.

He walked me to my car, which was nice, and wanted to kiss me. Frankly, when I was newly divorced, I probably would have kissed him, even without feeling any chemistry. Today things are different because I’ve already sowed all my wild oats. My flings are over, and now I’m looking for someone real.

I Know What I’m Looking for in a Man

Today I’m looking for a high-quality man who is interested in a true log-term relationship, not a guy to go on a casual date. There’s a difference between the two. Because I’m looking for a high-quality man, I need to be a high-value woman as well.

He asked me to text him when I got home, which I felt was thoughtful. And that was that. Bill was a great casual date, but nothing more. This is why clarity is so important. You really want to know what you’re looking for when you start dating. You may date less, but you exchange quantity for quality.

This is also why it’s so important to keep your options open. If I had pinned all my hopes on Bill, I could be second guessing myself, be tempted to settle, or be waiting with bated breath for his call. I’m not doing any of that.

Instead, my focus is on the men who I am dating a second or third time, and any new men that I add to my dating rotation. I focus on the positive and let the negative roll off my shoulders. I probably won’t remember Bill’s real name by tomorrow! And that’s perfectly okay. I was polite, kind, witty, and charming on our date, and he got his money’s worth.

If you want to date with more clarity and confidence, join the waitlist for my upcoming FREE elite masterclass, How to Find Love over 50 Without Ignoring Your Inner Self. We’ll be exploring the three dating mistakes all women over 50 make, the four ingredients you need to find love, and my inside/out – outside/in coaching system in dating coaching program.

Let’s Have a Conversation:

What expectations do you have on a first date with someone new? Where do you draw the boundary when it comes to a first date? How would you respond if a date told you to “Shut up”?