Dear Katherine,

For the first time in a long time I had a relationship where all I had to do was authentically be myself. I am a performer, and because I spend so much time performing, finding a person that I could just be with was amazing. Sadly, we broke up. He just wasn’t over his ex.

I haven’t found that sense of complete being with other partners since him. Does that mean I should just stop dating? I’m spending a lot of time on dating apps. At what point is it too much? Too much time, too much energy? I feel like I’m talking to 15 million people and none of them are interesting. Is it me? Am I expecting too much? Are the apps not geared to the individual that I’m looking for?



Over Dating

My Dearest,

My short answer is no. And yes.

I have often felt that I was wasting my time on dates. I’ve also felt that I was wasting the time of people that I sent out on dates who pay me, as a matchmaker, hundreds of dollars to do so. Why are we rushing around drinking gallons of beer and wine, talking to people who we barely know and may or may not be attracted to, eating food we can’t digest and clocking hours and hours on screens having conversations about subjects as banal as 90s television and that buffalo we once posed with in a national park?

Is this really how one finds meaningful connection? By getting so exhausted and frustrated and fed up that you’ll quit literally fall into the arms of the next person you meet who doesn’t smell like cheese and can hold up their end of a conversation?

No. And yet, yes.

Because you will also learn from meeting these people. There will be a moment when you are sitting across from somebody re-hashing Teenage Mutant Ninja Turtles when it occurs to you that you cannot WAIT to tell them about that one time you saw a buffalo at Yellowstone, or anything really, because they are listening to you and looking at you in a way that makes you feel “authentically yourself.”

You’ll never meet that person if you don’t leave your house.

I personally have spent most of the last three years doing some version of “leaving my house.” I, like you, have also been a performer and have found myself trying on various identities and ideologies. I sympathize with your feeling of dating burnout. If you are a subscriber to the “Fuck Yes or NO” line of thinking, engaging with people in superficial ways can feel like a slow death.

The Law of “Fuck Yes or No” states that when you want to get involved with someone new, in whatever capacity, they must inspire you to say “Fuck Yes” in order for you to proceed with them.

The Law of “Fuck Yes or No” also states that when you want to get involved with someone new, in whatever capacity, THEY must respond with a “Fuck Yes” in order for you to proceed with them.

There is only one approach: Don’t do it if it feels like it’s killing you.

From what I can surmise, most people fall in love maybe once every ten years. At best. And yet we believe that we should be in love all the time. And when you’re talking to 15 million people at once it feels like you SHOULD be in love with at least one of them. But really, it doesn’t work like that. You don’t feel like you’re in love and being your authentic self right now? That’s how most people feel most of the time. You’re in good company.

The reality of the situation is that that guy you loved so much is not your partner right now.

Sometimes dating feels really bad when we have a meaningful connection that was taken away from us against our will. You were deeply into this guy, and he called it off. That’s heartbreaking. Having somebody take that kind of attention away can feel like being abandoned. You can convince yourself that if you do certain things you will be able to get it back. That’s when we draft endless emails that they never reply to or show up at their houses late at night in our bathrobes asking them to love us or write a breakup album.

The truth is it never works. You don’t earn love, and you don’t win it. The sooner you are able to realize that you cannot control that person’s feelings about you, the freer you’ll be to move on.

A friend of mine said recently that he thought all humans should have “If you feel it, it’s fair” tattooed behind their eyelids. I’m inclined to agree with him. You don’t get to wallow forever, but if you’re feeling terrible you don’t have to fix that immediately.


Limit how much time you’re spending on these dating apps. Maybe just do it for an hour a day. Or 20 minutes three times a week. Remember the old food pyramid? Think of your time on dating sites as the “fats and sweets” triangle at the top. Fill the rest up the bottom tiers with things you really like doing.

When you are seeing people, strive for more in-person interaction. Invite people out sooner. If you see somebody you think is cute, ask them out in person. Allow your romantic life to be something that happens between you and other humans in person, not on a screen.

We often feel as though we have to arrive to a date as shiny, happy people. There’s something to be said for that, but at the same time I think it can be disingenuous. There’s a fine line between affability and repression. Next time you go on a date try saying exactly what you think and feel, and see how it goes. People often reflect back at you what you’re showing them, so if you present as honestly as possible you might find the people you’re talking to become more compelling. Here are some of the deeply weird things people have said to me on first dates:

“I have a very dark heart.”
“I would invite you over but I don’t have a bed.”
“All of Spain is special.”
“You have a perfect nose.”
“I will drive you to Alabama in my pickup truck to see your dead relatives.”

Taken out of context these people sound loony, but the truth is their honesty was deeply charming.

Do things you love, by yourself or with others. People say this all the time when it comes to dating. “If you love being outdoors, join an outdoor club!” I get sick of that. I’m not the kind of person who joins clubs. The truth is, we’re all too good for meet-up groups and strange organized social connection.

Do something cooler. How do you want people to gather together? If you could control it, in what circumstance would you want to meet somebody? How can you engineer that circumstance? What conditions make you feel “authentically yourself?” Create them.

You will feel loved and seen again. I can’t guarantee that, but it’s likely. Also, even if you don’t, it’s better to live your life like you will as opposed to worrying how you might not. When you do get that feeling again approach it with tenderness, care and openness. You’ll appreciate how rare and beautiful it really is. Love begets love.

Another friend of mine always says, “one door closes, another door opens, but it’s the hallways that are a bitch.” Dating apps are like those hallways. Stay as long as you need, learn what you can, and keep moving.

Just the Tips is’s weekly advice column, with professional matchmaker Katherine Cooper. Have a question for Katherine about sex, love or dating? Shoot her a note at