I’m impatient. I understand this about myself. After six months off-market, I’m a bit restless to be kissing and snuggling again. Not in a hurry, mind you, but intent.

How To Find the Patience for Dating

Here’s the thing. You’re going to swipe LEFT a lot. And those that you ambitiously swipe right on, are not going to respond. Welcome to online dating 2025. It’s okay, it’s just a bit more cautious, fueled by false idols promoted by celebrity beauty, glam, and plumped cheeks. No, no, no. My daughter gives me hell for not liking fake eyelashes. “Dad, you’re so old fashioned.” Yeah, I guess that’s true. I’m also willing to wait for “next.” I’m not sitting on the sidelines, but I am resetting my YES and NO lists. I’m trying to evolve my own dating strategy.

YES

• fit
• joyous
• smile
• has a passion that comes through their profile
• not alcohol or luxury-focused

NO

• obvious “work” of any kind
• too many margaritas
• your tats, your flags, or your motorcycle
• boob-first
• sunglasses in every shot
• trying to make up for years of unhealthy habits with creative photography

We’ve all seen the initial profile photo and said, “Damn!”

What Happens Next?

In some ways my first three “hello dates” provided a lot of information about me and about what I’m looking for. Also, reinforced my idea of talking on the phone first. We know photos and profiles lie. So, get to the chase quickly and get on the phone to see if there’s communication chemistry. Are they interested in your stories? Do they have stories? Does the conversation make you feel excited to meet or “meh?”

Getting to a “hello date” is the first step. In my experience, it takes some time. Put plenty of feelers and “hi there” messages out there and listen for what comes back. In my previous incarnations, I might have gone for volume over fit in my opening moves. Today, I’m just not interested in playing the field.

I want authentic. I want now. I want a connection.

In my first two greetings, I was underwhelmed by the energy. There was no vibe. On the third date, there was a significant YES going on for both of us. It was exciting to get a positive response from an attractive and interesting woman. We made second-date plans easily. I proposed dancing, since it was something she mentioned. On the country dance floor, I’m a bit out of my element. I should’ve waited until the “lesson night.” As it was, I was all left-feet. It was an odd feeling. I certainly noticed that I’d jumped off the high dive and was not enjoying the freefall. I was not into it. She was not as experienced as she might have led me to believe. She was still dangerously cute and I would’ve wished for a YES. What I learned was this: I might go country dancing with you, but it’s not my thing. Turns out, it wasn’t really hers either. We were seeking common ground.

Baby Steps in Online Dating

I began to explore my ideas about dating with this woman on our first ice cream date. She was new to the single market. I was date number one. Oh, boy!

Define some interests that you can share. If you don’t have any obvious links talk about things that excite you and see if the other person shares any flicker of enthusiasm. That’s what you want. An enthusiastic yes. I felt that might have been the case initially. The real stories begin to come out on the second date where you’re actually evaluating the potential. She told me a story that challenged my interest. I won’t go deep, but her husband of 36 years came out as gay. Apparently, they were big dancers back in the day. Um…

I am looking for someone who is fit and has ambitions beyond happy hours and travel. That seems to be a lot of the profiles. I mean, what do you say to someone who “likes long walks on the beach and wine paring?” Um.

I am looking for a woman who is comfortable with their life. Someone who’s mapped out a clear direction for themselves and would like a co-pilot, maybe like me. I don’t want someone to teach me how to love or be loved. I would like them to arrive knowing the how and why of their motivation. If it’s travel and beer, well…

Beyond the Second Date

I talked too much on the ice cream date. I should’ve listened more. I should probed a bit deeper into why she didn’t want to answer the “how long have you been divorced” question. Perhaps she’s not divorced. She might have just done a geographic relocation to sort out what’s next for her in the upside-down world.

At some point, you’re going to want to kiss. Ask. Confirm.

Then, feel. It is my emotional radar that gives me the best data. I felt her clam up when I asked about her divorce. The longer story came out over dinner a few nights later. It was a whopper. I was committed to dancing, but I might have cut it short and gone home. I sort of wanted to feel the dance floor, put my arm around her, and see where things led. Nowhere.

Here’s a paraphrase of what I said to her about dating. “At some point, if things go well, we’re going to want to kiss, see where that goes. Don’t worry, I’m not in a rush. Then, if things go really well, and we’re both feeling the desire to move closer, we’re going to orchestrate sex. That just means, for me, it’s not a casual thing. I’m looking for a LTR not a date or a bootie call. Nice when they happen, but preferably from someone you already love. Anyway, then, before we have sex, I’m going to be clear, ‘I am exclusive’ the minute I begin moving beyond first base.”

I don’t think I’d edit too much of that. But in the moment, I might have given her more time to catch up and tell more of her story. It was very vague. She seemed cheerful and eager. She was harboring a deep pain she wasn’t ready to share with anyone. It came out over dinner. I stayed with the plan. After a few dances and some chatting on the outside porch, it was obvious to me I was uncomfortable.

“I like that I’m off balance here,” I said. “This is really not my place.”

“It’s okay,” she said. That’s what she said to almost everything. But it was not okay.

“We should probably head out,” I said. “It’s eleven.” The dinner had gone long. I was fascinated by her story. Terrified by it as well. I guess I didn’t want to let her down. Odd to think about, at this point. I wanted to try country dancing again.

“What kind of dancing do you like?”

“I love going to see live music. Or funk. There are some funk dance nights around. But, I don’t really go out dancing. At least, not yet.”

It was a pleasant date. There was no talk of “what’s next.” I texted her the next morning. “We are just in different places in our lives.”

She agreed.

Regroup, Reboot, Recenter

I need the calm again. Remember what I’m in it for. Not sex. Not cute. Not money or luxury. Nope, just time.

Here are the facts.

I’m 62. I would like to date someone within 7 years on either side of my age. (No, not always younger!) At this point in life, I’d like some of life’s complications to be solved. I want to date someone who is looking forward not dragging a past of pain and unresolved anger. I have no complaints at the moment. My life is in order. Money, career, kids, ambition, I’ve got them in my pocket at this point. I’d like someone who is on the same page of life. That’s where age can get in the way if they are too young (what are our common connections) or too old (too tired to climb another mountain).

This dating thing, it’s like a long trek. I’ve been divorced for fourteen years. My kids are almost launched. I’ve remained intentional in my dating experience. And three LTRs later, I have a good idea of what I am looking for. Age is going to compete with us in all of our adventures. Dating is no different. Sure, the 40-somethings look great, but they’ve got SO MUCH to figure out. I want a woman who’s already figured most of it out, but now they want an engaged and vibrant partner to sail off into the sunset with. I’m not ready for the sunset years, I’m ready for adventure, even if it’s in companionship and relationship-building. I am all in.

Finally, give it 110%. With each relationship, I have learned primary things about myself and what I want. In all three of my LTR attempts, I put everything I had into building, crafting, negotiating, and grooving with another person. One other person. I’m not a serial dater. I’m also not settling for mediocrity. You shouldn’t either.