First Dates and 50-Something-Year-Old Men

My Problem with First Dates and Fifty-Something-Year-Old Men

Kerry McAvoy, Ph.D.

Problem First Dates

How to improve the art of conversation

A Recent First Date

As I recently stepped into an unfamiliar, upscale restaurant, I smiled at my date’s choice of venue for our first meeting. He chose the perfect place to get to know someone better.

The crowd was sparse for it being happy hour. Tabletops for four were scattered about the room. Soft music played in the background, and the murmuring of the clientele was low.

Looking around, I spied a man sitting alone. He was scanning the faces of those entering the restaurant. He seemed a bit older than his profile photo and a few pounds heavier. I readjusted my expectations and let it go.

I nodded to indicate I’d seen him. He got to his feet as I approached.

Here was the first awkward moment — do we shake hands, hug, or give a kiss on the cheek? I watched for any nonverbal cues to indicate his preference. He gave me a quick hug, not too close or too tight, and then took his seat once again.

Since we’ve been texting a few days, I knew a bit about him — where he worked, that he was divorced, and that his grown children were doing well.

Looking at him from across the table, I smiled and said, “Love this restaurant! Been here before?”

“Someone from work recommended it,” he answered. He returned a slight smile and looked down at the menu as we both let the initial rush of awkwardness pass.

Now, we’ve reached the second hurdle — who will take the lead of the conversation and what will be the first topic.

“You’ve been dating much?” he asked. I inwardly groaned. A potential trick question. Was he assessing the scope of his competition, wanting to share dating war stories, or checking in to see how I’m holding up with the challenging task of online dating?

I sidestepped it by answering, “It’s going okay. You?”

And thus started our first real conversation.

An Example of the Art of Conversation

Once in a while, the first dates go well. The conversation flows as each of us takes turns, asking a thoughtful or probing question. The conversational lead is like a ball we toss back and forth between us. Each person holds it briefly, before lopping it in the other person’s direction.

It looks something like this —

Date: “Tell me a bit about your work.”

Me: I’m a retired psychologist. I write full-time now.”

Date: “Oh? That’s a big change. How’d that come about?”

Me: “After counseling for over twenty years, I decided it was time to do something new. I discovered writing almost accidentally.”

This line of discussion continues for a few more minutes before I ask, “What about you? Tell me more about your work?”

And just like that, the spotlight shifts to the other person.

This example is how discourse is supposed to go between two people — in a back and forth motion, with each person taking a turn at being the center of attention.

We’ve Forgotten How to be Curious

However, I’ve discovered through my recent re-entry into the realm of dating that this rarely happens. Granted, I’m in my fifties now. The men I’ve been meeting have gone through some tough stuff. They may have experienced one or two divorces, or the death of a spouse. They’ve raised children, might have had a job shake-up, and moved a few times. Maybe there have been losses, rejections, or unwanted surprises.

All of this creates an opportunity for growth or for more hang-ups. I’ve learned firsthand I can approach life from a position of fear or curiosity.

Unfortunately, openness and curiosity seem to be a rarity among men my age.


Let’s pick back up with the first guy I described at the beginning of the article.

We met online, texted a couple of days, and had a lovely telephone conversation. We decided to meet up for dinner. My hopes were high.

Right after this guy asked if I’d been dating much, the conversation took a turn for the worst. He then proceeded to share what had gone wrong with all the previous women he’d met. Lumping me in without getting to know me, I heard how we, women, want too much from him, can’t accept him the way he is, and hide important details.

Defensive anger radiated from him as he repeated the same message two to three times. I nodded my head and offered sympathetic comments. I tried to steer the conversation into safer topics, only to have him revisit his grievances once again. This went on for nearly two hours before I stood and politely said I needed to go home.

I wish I could say my last date was an anomaly, but that experience has been the norm. Another suitor talked at me for two hours, except to take a bathroom break. He didn’t ask me one single question — not one.

Does Having Life Experiences Equate Being Self-Absorbed?

What’s happened? Where did the art of conversation go? We can’t all be this flagrantly narcissistic, can we?

Honestly? I’m discouraged. Where are a few good men who can show up emotionally? Who are genuinely interested in getting to know their partner?

Women aren’t perfect. I know that all too well. I’ve read several recent articles about the unreasonable expectations women have of men. Both sexes need to take responsibility for getting their shit together.

So what can we do to improve the first-time date experience? Here are a few suggestions:

For Men

  1. Relax, you don’t need to impress her. She already is interested or she wouldn’t have agreed to meet you.
  2. Use your nervous energy to help you focus. Channel it into positive interest.
  3. Remember the person you are meeting is someone new. If you have done your work to heal after the last breakup, she isn’t like your past girlfriend or wife.
  4. Monitor yourself and make sure you are giving her equal time to share the conversational floor. Keep your answers to a few sentences and then lop a question to her.
  5. Don’t put her on the spot at the end of the date by asking her if she would like to go with you again. Wait a few hours or until the next day to check in with her, but do check back in.
  6. Finally, don’t ghost her. If you aren’t interested in pursuing anything further, politely tell her so and wish her well.

For Women

  1. Avoid giving a list of your preferences, such as likes and dislikes in a guy. Keep an open mind by giving this person a chance before making a snap judgment based on superficialities.
  2. Ask yourself, how does it feel to be with this guy? Do you feel safe, respected, or admired? Or, are you uncomfortable, intimidated, or edgy? Listen to your gut; it’s your best friend. It will pick up nonverbal cues your conscious mind may miss.
  3. Know your boundaries and limitations before going on a date. Are you comfortable with any physical contact? If so, what kind and to what extent? What topics are okay to talk about and what’s best to wait until you know someone better. Stay within these guidelines, unless you can articulate to yourself a clear reason to break your own rule.
  4. Be blunt about your desires and needs. Women often use indirect communication to express themselves, whereas men are more likely to use direct. Don’t expect your date to read between the lines. If you aren’t interested, say so. If something is making you uncomfortable, speak up. If you want to leave, tell him. Don’t leave him guessing. Most likely he’ll get it wrong.

Maybe we need to readjust our expectations and agenda for the first date. To come into the experience with an open mind. To intentionally leave our leftover relationship garbage either at the therapist’s office or in the past where it belongs. Maybe we need to learn to approach the process of getting to know a potential romantic interest with curiosity.

Maybe we need to learn to listen more and to talk less.

As for me, over a week ago I decided to take a break. I’m going in a different direction and have hired a matchmaking service. I’ll let the matchmaker vet my dates so I don’t have to. Let’s see if that works any better.

Interested in learning who I’m using for Matchmaking Services?

Check out Tawkify!


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