What Is Datemaking? Why We Need to Start Going on Dates Again

Since starting Real Dates, I've spent a lot of time talking to single people about dating.

I've heard about the apps, the bad dates, the dates that never happened, the endless conversations that went nowhere and the frustration of trying to meet someone when you're also trying to have a career, maintain friendships and live your life.

But something else kept coming up.

People just aren't going on that many dates.

They're looking. They're talking. They're thinking about dating. They're trying to figure out who might be right for them.

They're just not meeting enough people.

Dating apps, matchmaking services and even our own lists of what we're looking for have given us more ways than ever to search for the right person. The more conversations I had, the more I started thinking that maybe we have put so much emphasis on finding the right match that we've forgotten how important the actual date is.

That's where the idea of Datemaking started.

We Put a Lot of Pressure on a Match

Think about how much we're expected to know about someone before sitting down with them for a drink or dinner.

We look at photos. Careers. Education. Interests. Where they live. What they're looking for. Whether they check the boxes we've decided matter.

Sometimes all of that information is helpful. Of course I want to know enough about two people to believe there's a reason they should meet. That's a big part of what I do.

Traditional matchmaking puts a lot of emphasis on finding the right match, and for good reason. Compatibility matters. I just think there's another part of the equation that deserves more attention.

Actually getting people on dates.

I've met people who sound great on paper and feel completely different when you're talking to them.

We've all had the opposite experience too. Someone becomes more attractive as you get to know them. They're funny in a way that doesn't translate to a profile. There's something about their personality, their confidence or their energy that catches you off guard.

You can't put all of that into a questionnaire.

At some point, you have to meet.

Chemistry Happens Across the Table

This has become one of the things I believe most strongly about dating.

We can make thoughtful introductions. We can look for compatibility. We can pay attention to the things that matter to someone.

Then two people sit down together and something happens.

Or it doesn't.

That's the part nobody can promise.

Chemistry lives in the conversation. It's in the laugh you weren't expecting. The eye contact. The story that makes you want to ask another question. The feeling that dinner has been going for two hours when it feels like 30 minutes.

I don't think we should be afraid of not knowing whether that's going to happen.

I think that's one of the best parts of dating.

A match is a possibility. A date is an experience.

And we need more of the experience.

What Is Datemaking?

Datemaking is the practice of thoughtfully bringing two people together and creating the opportunity for real life chemistry to happen.

It grew out of a pretty simple belief.

If two good people have enough in common that there could be something there, give them the opportunity to find out.

Make the introduction. Get the date on the calendar. Pick a great place. Take away some of the friction that makes dating feel like another thing on the to do list.

Then go have dinner.

That's really where the answer is anyway.

The Datemaking approach still values compatibility, standards and thoughtful introductions. I spend a lot of time getting to know people and thinking about who should meet.

I also think we've become so focused on trying to predict the outcome that we've made going on a first date feel much bigger than it needs to be.

A first date is a couple of hours with another person.

You might really like them.

You might not.

You might be surprised.

That's why you go.

I Think We've Been Too Hard on the Date

There's another part of Datemaking that has become increasingly important to me.

Somewhere along the way, we started measuring the value of a date by what happened afterward.

No second date? It didn't work.

No relationship? Another bad dating story.

I don't see it that way.

You got dressed. You left the house. You went somewhere. You met someone you wouldn't have met otherwise. You had a conversation.

Maybe you learned something about what you're looking for.

Maybe you realized something you thought mattered to you really doesn't.

Maybe you had a great dinner with a perfectly nice person and knew by dessert that you never needed to see each other again.

That's okay.

There is value in going out and experiencing people.

There is value in getting comfortable sitting across from someone new.

There is value in being part of your city and your life instead of waiting until the perfect person appears.

And yes, eventually there is the possibility that you sit down for one of those dates and something feels different.

You can't get to that one without going on the others.

Dating Is a Muscle

I hear from professionals all the time who haven't been on a date in months. Sometimes longer.

Life happens.

You work. You have your routines. Your friends get married. Going out changes. Staying home gets easier.

Then dating starts to feel intimidating because you haven't done it in a while.

I think dating is a little like a muscle.

You get more comfortable meeting people by meeting people. You become a better conversationalist by having conversations. You learn what you're drawn to by experiencing different personalities in real life.

You build confidence by showing up.

That matters whether the person sitting across from you becomes your partner or someone you never see again.

There is something bigger here too.

Going on a date means there's something on your calendar. You're getting dressed. You're trying a restaurant. You're meeting someone new. You're experiencing your city and participating in your own life.

I think a lot of us could use more of that.

What Does a Datemaker Do?

When I started Real Dates, I called myself a Tampa matchmaker because that's the word everyone understands.

But the longer I've done this, the more I've thought about what I really want my role to be.

I care about the match. I spend time getting to know people and thinking about who I believe they should meet. Personal matchmaking is still very much part of what happens at Real Dates.

But I also want to get people out.

I want to put something on their calendar that they're excited about.

I want them to walk into a great restaurant, sit across from someone new and have the chance to feel something they couldn't have predicted beforehand.

I want people to experience dating again.

So I've started calling myself a Datemaker.

A Datemaker is someone who thoughtfully brings people together, gets the date on the calendar and creates the opportunity for connection to happen in real life.

That better describes what I'm trying to do.

I can make the introduction. I can plan the date. I can create a good opportunity.

Then I have to let two people figure out what happens next.

Let's Get People Dating Again

I don't know who you're going to fall in love with.

I don't think anyone really does.

What I do know is that it's very hard to meet that person when you're not meeting anyone.

So maybe we can take a little pressure off the first date.

Go meet someone who seems worth meeting.

Have dinner. Ask questions. Laugh. Be curious. Give someone a chance to surprise you.

If there's chemistry, see them again.

If there isn't, wish them well and go on another date.

Because somewhere in all of those dinners, conversations, awkward moments, surprises and nights you almost talked yourself out of, something can happen.

You start dating again.

You start experiencing people again.

You start experiencing life again.

And eventually, one of those dates just might be different.

That's Datemaking.