How to Answer the Question You Dread Most on Dates

Debbie is 42. She went to an Ivy League school. She’s an entrepreneur who makes hundreds of thousands of dollars a year offering bespoke services for her high-end clientele. 

On the other hand, she had a bad family upbringing, she’s never been married, and she has no kids. 

Debbie’s story is not that unusual. Lots of women who had dysfunctional families grew up to be overachievers – to try to control their own destiny. Similarly, lots of them never found peace in their relationships because they were drawn to partners who resembled their toxic parents. 

Debbie’s dilemma wasn’t whether she was smart, attractive, kind, or had a great personality. She knows her worth in life. Her insecurity is strictly about her inability to tell her story from a place of confidence when she meets new men. 

The operative word here is shame. Even the most competent people have a level of embarrassment about their failures, especially ones they haven’t yet overcome.

Over the years, I’ve counseled women who have overcome sexual abuse, have been divorced three times, have had kids out of wedlock, are recovering alcoholics, have a history of mental and physical illness. All of them have the same concern: how do I tell my story without it being a total turn-off that drives every man to run in the other direction?

Today, I have an answer for you.

It’s a formula. I call it the Politician Speech. It’s basically the same answer you’d expect to get from a candidate in a presidential debate when they receive a tough question.

In this case, the tough question is: “why are you still single?” or “What happened with your last relationship?” A question so utterly predictable that leaves you feeling anxious. 

You may think questions like this are like an attack, as if a stranger across the table is trying to judge you. That couldn’t be further from the case. In fact, if you’re on a date, that person probably likes you and has no understanding how you ended up at dinner with them.

Getting mad, defensive, or shutting down is the absolute WRONG way to handle these benign yet uncomfortable questions. 

Here are the elements to a successful Politician Speech. 

1. You need to have a good relationship with your own story. If you’re still in pain about it, it’s hard to talk about it. If you’ve processed your pain and can see it from a distance, it’s a story of triumph. 
2. You need to tell the truth. This is why “I just haven’t met the right person” is such a lame answer to “why are you still single?” It’s not that it’s false. It’s that it doesn’t take any responsibility for WHY you haven’t met the right person. 
3. You need to add a measure of self-awareness and growth. It’s one thing to talk about struggles you’ve had; what your date wants to know is whether you’re past them or if your issues are still going to present a problem. 
4. You need to end on a high note. Just like any feel-good story, you want the person listening to feel positive about you so they can see a path to success. 

Naturally, I figured this out from my own struggles. Remember, before I was a happily married dating coach, I was pretty much a mess. 

Despite my healthy background, my drive, and my writing skills, at age 30, I was depressed, unemployed, anxious. I put all my energy into being a Hollywood screenwriter and I failed. It was impossible to have those failures not affect my mood or feelings about myself. One date even said that I didn’t need a girlfriend; I needed a shrink. She was right.

Then, at 31, I wrote a book and started dating coaching, in spite of the fact that I was still very much single. 

Now imagine trying to tell my story on a date – a 34-year-old man who has never had a real job, has been on 300 dates, and has never had a girlfriend for more than 8 months.  

“So, Evan, why are you still single?”

“It’s funny you should ask that. I’ve spent an inordinate amount of time thinking about it myself. I think it’s charitable to say that I was a mess in my 20’s. I came to Hollywood to write screenplays when all of my other friends from Duke were lawyers and bankers. And although I came really close to success a bunch of times – agents, managers, meetings at studios, etc – I never made enough to be a full-time writer. 

And at some point, I had to admit that my dream was making me miserable and I had to pivot. Went to film school, got a job answering phones at JDate, and wrote a book about online dating and the next thing I know, I had some success. And I guess, for a few years, I was really enjoying that success – making money for the first time, dating prolifically online. 

But after coaching people on the phone, I realized I was a hypocrite: I was giving advice I wasn’t following. I was overvaluing looks and undervaluing character and communication skills. Now I’m at the point where I’m truly excited to get married and begin a family – and I’ve never been in a better position to do so.”

I hope you can see that this is a story of a guy who can reflect on what he did wrong, explain how he learned from his mistakes, and was truly ready for love. 

If we look at Debbie’s story – or yours – it wouldn’t be too hard to put together something similar:

“I grew up in a highly dysfunctional family where my Dad had a temper and I never felt safe with him, so I put all my energies into my studies and career. 

When I did get into relationships, they were usually with men who were great on paper. Impressive. Intelligent. Fit. But they were usually missing the emotional component and I would invariably stay for 5 years when I probably should have left in a year. 

In between, I spent a lot of time building up my career and have a business that, in the past, required almost 24/7 devotion, which pulled me further from healthy integrated relationships.

But in the past few years, I figured out that I could have better work/life balance and have recently recalibrated my schedule to open up more time for love. And, more importantly, I learned not to ignore incompatibilities for months and years just to try to make things work when they’re not working. 

So basically, you’re the beneficiary of my previous 42 years of getting things wrong. Lucky you!”

Debbie sounds effortlessly confident, positive, and optimistic despite having a rough upbringing, never getting married, and never having kids.

Whatever you’ve been through may be painful but if you’ve learned your lessons, you can incorporate them into your story, and turn your weakness into a strength.

Love,

Evan

* This article was originally published here