5 Smart First Date Tips for Singles Over 60

As I’m writing this, it’s finally looking like the pandemic may be behind us in a few months. I’m hopeful that any of you holding off on dating all this time will be able to get back out there, and meet people in person soon.

When I was getting ready for my first date with Cosmo, I was a little jittery . . . not terribly nervous, but somewhat anxious.

We had met on a dating site, exchanged a handful of emails and a phone call or two leading up to the date.

A year and a half of other first dates preceded the one I had with Cosmo. I had gotten pretty good at it by then.

For the most part, I didn’t waver from my dating plan. I stuck with the tried and true dating do’s and don’ts that worked for me.

5 Smart First Date Tips To Make Your First Dates More Enjoyable, Safe and Successful

1. Don’t rule someone out based on frivolous things but, at the same time, pay attention to your first impression of them.

This is a tricky thing to navigate.

You want to be fair and give people the benefit of the doubt. On the other hand, you don’t want to encourage someone you’re pretty sure isn’t right for you.

For instance, you don’t want to dismiss someone because:

• They have a hard time making small talk.
• They’re so nervous they blather on and on.
• They’re 5-10 minutes late.
• You’re only mildly attracted to them.
• You dislike the way they’re dressed.

Give them a break. First dates are extremely nerve-racking for some, especially if they’re new to dating.

Then again, remember that most people put their best foot forward (in appearance and manner) on a first date. If that best foot leaves much to be desired, what’s going to happen on dates two, three, four and beyond, when most people ease up, and pay less and less attention to the details.

You may want to think twice about them if, on the first date:

• They’re dressed like a slob, have bad breath and don’t smell so good.
• They ask you very little about yourself and seem disinterested when you speak.
• They’re mean-spirited when talking about their friends, families, co-workers, employees, etc.
• They can’t stop laying into their ex.
• They answer cell phone calls when there’s no emergency situation pending. They don’t want to miss a call.
• They’re rude or overly demanding to the wait staff.
• In general, you don’t get a good vibe from them.

And do a little homework beforehand. Go back to the work you did identifying who your ideal partner will be.

2. Meet them for coffee, instead of a meal. And don’t have them come to your house to pick you up.

No matter how great your initial communications went, you really don’t know this person . . . even if someone you know has introduced them to you.

There are a number of reasons not to go to dinner on a first date, including:

• Dinner typically lasts an hour or longer. If things aren’t going well, you’re probably stuck with them until the dessert menus come around.
• Most times of year, it will be dark when you’re done with dinner. Do you want to have a stranger walk with you to your car in the dark?
• Dinner is a relatively big investment to make for a potential first-and-only date. Neither of you should be expected to shell out that kind of money for all the first dates you’re likely to have, if you’re seriously dating.

Even lunch can pose problems. You want to be able to ease out the door quickly, if things don’t work out.

That’s the beauty of just going for coffee.

And make it some place like Panera, where you serve yourself and won’t have to wait for someone to bring you a check. If things are going well, you can linger. If not, you can leave quickly.

Do I need to elaborate on why having a stranger come to your home and/or get in the car with you is a very bad idea?

If someone pushes you to do either of those things, or insists on going to dinner, even though you’ve made it clear you don’t want to, that’s a pretty good indication of their character, isn’t it?

3. Drink very little alcohol, if any, on a first date.

I hope the downside to drinking on the first date is obvious. Again, you don’t know this person, so you shouldn’t make yourself vulnerable or risk making bad decisions.

Although having a drink may help ease your nerves, it will also help loosen your conversation and inhibitions.

After even 2 drinks, you’re much more likely to say or do things you’ll regret.

On a first date, you’ll want to be clear-headed so you can assess this person. Alcohol may make someone who’s all wrong for you seem all right for you . . . especially if they’re someone very attractive.

I suppose one drink isn’t going to hurt, but I feel that NO drinks is wiser. Cosmo agrees.

All the more reason to meet for coffee on a first date. A coffee shop probably won’t serve alcohol. No one will be tempted.

4. Prepare some questions and small talk for your first date.

If you met them on a dating site, reread their profile and jot down a few things to discuss. If you exchanged a few emails and had a phone call or two before setting the date, refer to those experiences.

Use your questions to break the ice, if needed, and keep a balanced conversation going.

But don’t go overboard and inundate them with questions.

I remember a first date with a very nice man who was anxious to please, but very nervous.

We were having a pleasant conversation when he suddenly pulled out a sheet of paper with about a dozen questions on it, and began drilling me from his list.

Things were going okay before that. We were chatting back and forth, so I was surprised he felt the need to interject with canned questions.

I had already decided we weren’t right for each other – for a number of reasons – so what he did didn’t have much impact either way. I mean, I always gave leeway when my date was nervous. You can’t fault someone for that.

Also, besides planning what to ask your date, think about some things you want to tell them about you.

Mostly, keep the conversation light and breezy.

Don’t get into comparing war stories about your exes. That makes for a negative vibe between you. If your date can’t stop themself from lashing out at their ex, refer to #1 above. They may not be over their ex, and ready to let someone new into their life.

5. Don’t write someone off because you don’t feel instant, explosive chemistry on date one.

I was lucky.

When I first met Cosmo, I felt that instant physical and emotional attraction I imagine most of us are hoping for.

Not just because he’s handsome, though that is a bonus.

And not just because he made such a great first impression on me, wearing body-hugging jeans, a crisp white oxford shirt and fitted suit jacket. Wow!

His many fine qualities were quickly evident. He met the most important criteria for my ideal partner. In particular, he was truly kind.

I could see right away that our values, sensibilities, interests and lifestyles were in sync.

When I first met Sam, with whom I had a happy 3-year relationship before meeting Cosmo, I wasn’t so strongly attracted, although he was handsome and personable. But I could see he was smitten with me.

So I went with that because I liked a number of things about him. Certainly enough to go on a second date.

I became more and more attracted to him, as we spent time together, and as I began to appreciate more and more what kind of person he was. Within a month or so, I was head over heels for him.

As I’ve written many times on this site, Sam died suddenly. When I was ready to start dating again, I kept that initial feeling I had for him in my thoughts, as I moved through all the first dates that led me to Cosmo.

If I had experienced something similar – liking someone, but not being bowled over by them initially – I knew that I would go on more dates with them, and see how things played out.

On the other hand, when a date raised red flags or displayed character traits that were deal breakers for me, I rarely went on a second date. Often when I did, my first bad impression was confirmed and I knew I should rule them out.