15 Questions I Probably Shouldn't Answer

I spend a lot of time writing about relationships, dating, love and the spectacular number of ways we manage to screw all of them up.

Usually, I get to choose the subject.

This time, I am sharing the top 15 questions I have received since publishing my book.

Some are about relationships. Some are about me. A few probably should have remained unanswered.

So naturally, I answered all 15.

1. How quickly have you known a date was going badly?

Seven minutes.

Maybe six.

We hadn't ordered yet.

She looked at me and said:

"You remind me so much of my ex-husband."

There are sentences you want to hear on a first date.

This isn't one of them.

"Good ex-husband or bad ex-husband?"

Apparently this was an excellent question because it launched a presentation.

He was selfish.

Emotionally unavailable.

Worked too much.

Didn't listen.

Had intimacy issues.

By the time the appetizers arrived, I fucking hated this guy.

Then something disturbing happened.

I started defending him.

"Well, maybe when he said he needed space..."

She stared at me.

I'd somehow taken his side.

A man I'd never met.

Against the woman I was trying to sleep with.

This is why I don't teach dating seminars.

She eventually started crying.

Then she went to the bathroom.

And called him.

At this point, I began to suspect the evening wasn't going particularly well.

She came back and said:

"I'm sorry. I'm just not ready to date."

I said, "That's okay."

And it actually was.

Because sometimes a bad date gives you exactly what you need:

Clarity.

She wasn't over her ex.

I apparently had developed sympathy for him.

And neither of us needed dessert.

I paid the check.

We hugged goodbye.

And somewhere in New York, a man I'd never met had absolutely no idea I'd spent the evening fighting for him.

You're welcome, buddy.

2. Have you ever stayed in a relationship you knew wasn't right?

Of course.

I'm a relationship author, not a relationship expert.

There's a difference.

I've stayed because I loved someone.

I've stayed because I thought things would change.

I've stayed because leaving felt worse than staying.

I've stayed because I said I would.

And I've stayed because the human brain has this remarkable ability to collect 47 pieces of evidence that something isn't working and conclude:

"Let's give it another week."

Then another.

Then Christmas is coming.

Then you already bought the tickets.

Then her birthday is next month.

Suddenly you've lost three years because nobody wanted to ruin Thanksgiving.

I've rarely regretted loving someone too long.

I have regretted how much of myself I sometimes gave away trying to make love enough.

3. What's something women are surprised to learn about you?

I have a pillow.

Not a type of pillow.

A pillow.

One very specific, old, ratty pillow. It is part of me. There can be six beautiful goose-down pillows on the bed and I'll immediately locate the one that looks like it survived the Normandy invasion. That's mine. A woman once picked it up and said: "Why don't you throw this thing away?" I remember thinking:

Well, this probably isn't going to work.

People talk about shared values in relationships. Apparently this is one of mine.

4. What's the most ridiculous thing you've done after a breakup?

That is an extremely competitive category. I'm not a good breaker-upper. Some people meditate. Some people travel. Some people spend six months working on themselves. I got a dog. I told myself I wanted companionship.

What I actually wanted was a living creature legally incapable of saying:

"I think we need to talk."

Her name is Charlie. It worked.

She's been considerably more expensive than therapy, has eaten several things belonging to women I've dated, and has absolutely no respect for personal boundaries. But she's never once asked me where the relationship was going. She even lost her mom after one of my breakups and didn't hold a grudge. My kids were still pissed at me years after my divorce. Charlie apparently processes abandonment better than humans. Or she's waiting until I die to write her book.

5. What's your biggest dating red flag?

I used to have a list. Now I have one:

How do I feel when I'm around this person?

Not: How attractive is she? Not: How interesting is she? Not: Is the chemistry incredible? Do I feel like myself? Because I've had relationships with enormous chemistry where I spent half my time wondering what the hell was happening. At some point, that's not chemistry.

That's anxiety with really good marketing.

At some point, butterflies stop being romantic.

Sometimes your stomach is trying to tell you something.

6. What's something you're embarrassed to admit?

I write everything down.

Everything.

Especially when a relationship is ending.

Most people deal with a breakup by talking to friends, going to therapy or drinking too much.

I apparently prepare a white paper.

I'll sit down and write pages about what happened.

What I did wrong.

What she did wrong.

What we both could have done differently.

What I learned.

What she should learn.

Why we loved each other.

Why love wasn't enough.

There are themes.

There are conclusions.

I'm surprised I haven't added footnotes.

And here's the embarrassing part.

Sometimes I send it to her.

At the time, I'm convinced I'm sharing something incredibly thoughtful and emotionally evolved.

"Maybe this will help her understand."

I'm sure that's exactly what every woman wants after breaking up with a man: his 4,000-word analysis of the breakup.

She probably opens it expecting, "I'll miss you." Instead she gets the Warren Commission Report. And the worst part is that I'll reread it before sending it and think:

This is really good.

It isn't. It's drivel written by a man whose heart is broken and who has temporarily confused emotional processing with publishing. I tell myself I'm looking for closure. Apparently my version of closure requires an executive summary. I'm working on it. I haven't written anything about it yet, but I might.

7. What's the loneliest you've ever felt?

Oddly, not when I was alone. I've been alone and perfectly happy. The loneliest I've ever felt has been lying beside someone I loved while knowing something between us had changed. There's a particular kind of loneliness in being six inches away from the person you want to spend the rest of your life with and feeling like they're a thousand miles away. It's even worse when you know they love you too, but for whatever reason, they can't talk about it. You want to shake them.

You want to fix it.

You want them to want to fix it.

Eventually you learn those are three very different things.

There's no joke for that one.

I'll leave it there.

8. What's something you believed at 30 that you don't believe anymore?

That finding the right person was the hard part.

It isn't.

There are amazing people everywhere.

I live in New York City. More than eight million people live here.

I find it hard to believe that all the good ones have somehow been taken.

Walk one block and you'll pass someone funny, intelligent, beautiful, complicated, slightly damaged and probably carrying a prescription.

That's New York.

Someone with an entire life you know absolutely nothing about.

Someone waiting to be understood.

Finding someone isn't the hard part.

Staying two people worth finding is the hard part.

That's the part I think we underestimate.

People change.

Bodies change.

Careers change.

Families change.

One day you're drinking wine in Paris.

Five years later you're standing in the kitchen asking why one human being needs every light in the apartment turned on simultaneously.

Both are the relationship.

Paris is easy.

Tuesday is the test.

9. What's the best thing about getting older?

I care much less about being impressive.

That's enormously freeing.

When I was younger, how people perceived me was paramount.

I had an image to uphold.

I worried about what complete strangers thought about me.

Think about how insane that is.

"I hope that man I've never met and will never see again approves of my life choices."

Now?

I want people I can laugh with.

A home I want to come back to.

A dog who's happy to see me.

A really good Burgundy.

My terrible pillow.

And a partner who says what she feels, means it, and then shows it.

You'd think that last one would be easier to find than a great Burgundy.

It isn't.

The list got shorter.

The life got better.

10. Do you still believe in love after everything you've been through?

More than I used to.

Just differently.

I don't believe someone completes you.

That sounds exhausting for them.

I don't believe there's only one person for you.

With eight billion people on Earth, that would be a spectacularly inefficient system.

And I definitely don't believe love automatically makes a relationship work.

I've watched things end that I desperately wanted to keep.

And every time, eventually, life put something incredible into the empty space that I couldn't have imagined while I was grieving what had been there.

Sometimes another person.

Sometimes a different life.

Sometimes a better version of me. But always, something better!

So yes.

I believe in love.

I just no longer believe I get to dictate exactly how it arrives.

Leave the door open.

You haven't met everyone yet.

11. Have you ever wanted an ex back?

Yes.

I've also constructed incredibly persuasive arguments in my head explaining why she should want me back.

She wasn't there for any of them, which hurt their effectiveness considerably.

Of course I've wanted an ex back.

I've missed someone while simultaneously knowing the relationship wasn't working.

That's the fucked-up part.

Both things can be true.

You can love someone.

Miss them terribly.

Know they love you.

And still be completely incapable of building a functioning relationship together.

Love alone isn't going to build it.

Two people have to show up.

Two people have to communicate.

Two people have to want to fight for it.

I've learned you can leave the door open.

What you can't do is spend your life standing in the doorway yelling:

"ANY DAY NOW WOULD BE GREAT."

Sometimes they don't wake up.

Eventually, you have to go live your life.

12. Do you write blogs to support your book?

This is a funny question, because I have started journaling again every night before bed. The reason is because my brain moves too fast.

Writing makes it slow down.

In my head, everything arrives at once, whereas others take a few more inputs to absorb a concept.

What happened.

What I think happened.

What I wish had happened.

What I should have said.

What she should have said.

What I'm afraid it means.

And, usually, three completely unrelated things I need to do tomorrow.

Writing forces all of that through a much smaller door.

One thought at a time.

And something interesting happens when I do that.

The story changes.

Not the facts.

My story about the facts.

That's an uncomfortable distinction.

Because we're all incredibly reliable narrators when we're the ones telling the story.

I was misunderstood.

I was trying.

I had good intentions.

They pulled away.

They didn't communicate.

Then I start writing.

And somewhere around page three, the prosecution begins presenting evidence.

I see the conversation differently.

I remember the thing I said before the thing she said.

I notice the pattern I couldn't see while I was busy being inside it.

Sometimes I realize I was right.

Sometimes I realize she was right.

The really annoying days are when I realize we both were.

That's what writing does for me.

It puts just enough distance between me and my life that I can turn around and look at it.

And sometimes I don't particularly like the guy standing there.

But at least I can see him.

Maybe that's why I write so much.

I'm not really trying to explain my life to other people.

I'm trying to understand it before my brain turns it into a story where I was right all along.

Although, given enough pages, I'm usually able to make a pretty compelling case.

13. What would the people who know you best say is your most annoying quality?

This feels like a question they should answer.

I'm sure there's a list.

I ask too many questions.

I overthink everything.

I want to understand why.

Why did you say that?

Why do you feel that way?

What changed?

What does that mean?

Most people can apparently accept an answer and move on with their lives.

I treat it like the first round of discovery.

"Nothing's wrong."

Interesting.

Let's spend the next 45 minutes exploring "nothing."

I'm also a fixer.

Tell me you have a problem and, while you're still explaining how it makes you feel, I'm already three exits down the highway building a solution.

Apparently sometimes people don't want a solution.

This remains baffling to me.

But if I had to guess what annoys the people closest to me most, it's probably that I have a very difficult time leaving things unresolved.

A conversation.

A disagreement.

A relationship.

A question.

I want to get to the bottom of it.

Which sounds like a wonderful quality until you're the person I'm trying to get to the bottom of.

I'm sure my kids could add considerably more to this answer.

They have my number.

Literally and figuratively.

Fortunately, I pay the phone bill, so there's only so much criticism I'm prepared to accept.

14. What do you fear the most?

Heights.

I know.

This requires some explanation.

I've jumped out of plenty of perfectly good airplanes.

I've done it with a parachute.

I've done it in a wingsuit.

Apparently jumping out of an airplane at 13,000 feet dressed like a flying squirrel seems perfectly reasonable to me.

Put me near the edge of a six-story building?

Absolutely fucking not.

I have a very specific problem with what I call the in-between heights.

High enough that if you fall, you're probably not surviving.

But not high enough to give a wingsuit enough lift to actually fly.

That's the danger zone.

A plane at 13,000 feet?

I'm good.

A roof deck at 60 feet?

We're going to need to talk about the railing.

I understand that none of this makes sense.

Fear rarely submits itself for peer review.

But at 13,000 feet, I have a parachute, a wingsuit and a plan.

At 60 feet, I have a cocktail and some contractor's interpretation of the building code.

I'll take the airplane.

15. Are you actually happy?

That's a dangerous question and, ironically, something my ex-wife asked me yesterday.

Because for most of my life, I thought happiness was something I was about to achieve.

After I made more money.

After the next business worked.

After I found the right woman.

After I bought the thing I was convinced I needed.

After I fixed whatever was currently bothering me.

I spent an extraordinary amount of my life being almost happy.

Which, looking back, is a pretty shitty way to spend a life.

Now?

Yeah.

I think I am.

Not because everything worked out.

A lot didn't.

I recently watched a relationship end with someone I thought would be the last face I'd ever wake up to.

Turns out I remain terrible at predicting the future.

I've hurt people I love.

I've had businesses fail.

Relationships end.

I've made spectacularly bad decisions with complete confidence.

And there are still things I want that I don't have.

But somewhere along the way, I stopped requiring my life to be finished before I could enjoy it.

I have kids I love.

Friends I can call, not see, because they live an ocean away.

Work that still excites me.

A home that feels like mine.

And I experience something new everyday.

And Charlie.

Good health, kinda.

A bottle of Burgundy I'm probably saving for an occasion that apparently hasn't happened yet.

And I'm still capable of falling completely, irrationally, inconveniently in love and I love that for me, because I am a hopeless romantic.

So yes.

I'm happy.

I just wish I'd figured out sooner that happiness wasn't waiting for me somewhere.

It was the shit I kept walking past trying to get there.

Paul Harkins