For some of us, It’s spring break. Dating While Gray producer Steve Lack is away for a conference and networking event.  Me, I’m screwing up my courage … to get back on the dating apps. After nine months in a new city, don’t you think it’s time?

I vow to give it a good go.  And if I stick with it longer than a couple of weeks, it will really be the first time I’m online dating with the hair color given to me by my ancestors, and time.  

With that in mind, we’re bringing you an encore episode of Speed Dating While Gray. You’ll hear a matchmaker’s unsolicited opinion about my chances of romantic success based on hair color. 

Is she right? Promise I’ll let you know what happens. Meanwhile, take a listen. And we’ll be back next week, with an all-new episode of Dating While Gray.

Headshot from 2017, with brown lowlights (Jenifer Morris Photography)

The final time I added brown lowlights, February 2021 (Jenifer Morris Photography)

Transcript

LAURA STASSI

Whenever I interview someone, my final question is something along the lines of, what else do I need to know? Or, what else would you like to tell me? Some people then bring up something they initially thought wasn’t relevant, and we go down an interesting new path.

So when I talked with D.C.-area matchmaker Michelle Jacoby for the podcast episode on romantic age gaps, we chatted for about 30 minutes on that topic. And then I asked her the question. Anything else? There was! We spent another 10 minutes or so talking about Michelle’s business and dating in general. And when that conversation wrapped up, I asked her again.

LAURA STASSI

Okay, is there anything else I need to know?

MICHELLE JACOBY

Well, we could sit and talk for days and days and days about all aspects of dating. But I can’t think of any.

LAURA STASSI

So I turned off my recorder and took off my headphones, I unplugged and unclamp the microphones, and stuffed everything into my equipment bag that I then slung over my shoulder. We walked from the sitting room in her rambling house to the front door, stopped there and I said, thanks again; I’ll be in touch.

That’s what Michelle said something so provocative, I knew that this interview wasn’t over. She agreed to return to the sitting room so that I could set up my equipment again and get her final comment on tape.

LAURA STASSI

You said something about my hair.

MICHELLE JACOBY

I think it’s beautiful.

LAURA STASSI

However …

MICHELLE JACOBY

Well, because you’re a single woman and you might at some point consider dating, I wanted — I like to say I’m a truth teller, and that — first of all, I think you’re absolutely beautiful.

LAURA STASSI

You don’t have to say that.

MICHELLE JACOBY

I know I don’t need to say this. But I want to say this because you — and you look stunning with your hair gray. But I think it’s important for you to know that you’ll probably have more options when you’re dating, in terms of more men who are interested, if you dye your hair. And that might sound annoying. But my job is to tell you …

LAURA STASSI

Yeah, no.

MICHELLE JACOBY

… exactly what’s going to help you be successful. And I can tell you a story about a woman who I worked with years ago, she was in her early 60s. And she had beautiful gray hair. And she loved it. And she felt beautiful. And I felt like it was my responsibility just to give her this information. She wants to keep her hair gray. That’s fine with me. But I thought she’d have many more options, and she really, really wanted to find a partner. But she was adamant that she was not going to change. Her hair was almost like her thing. Like, she just loved it. And I loved it too. But what I did is, I went through — there was an app or something where you can change your hair. So I took a picture of her, and I changed her hair to brunette. And I sent it to her just so she could see.

My phone rang so fast. It really did. She’s like, oh my god, I look 20 years younger. And she dyed her hair. I didn’t expect her to, I just wanted to show her the difference.

LAURA STASSI

Yeah.

MICHELLE JACOBY

And she fell in love with a man who was the same age as her and lived happily ever after.

LAURA STASSI

But, but then she had to keep her hair dyed.

MICHELLE JACOBY

Right. But here’s the thing, I always tell people look, I want you to be authentically yourself. But it doesn’t mean you can’t be strategic.

LAURA STASSI

Oh!

MICHELLE JACOBY

You know what? Showing up in your business suit is not strategic, I would show up in a cute dress.

LAURA STASSI

Yeah.

MICHELLE JACOBY

Femininity is your superpower.

LAURA STASSI

Right.

MICHELLE JACOBY

So there are different versions of us. There’s the mom version. There’s the sister version, there’s the neighbor version, the, you know, boss or employer version, the work version, and then there’s the I’m-dating-and-looking-for-my-partner version. And so sometimes you have to think about what’s going to increase your chances of being successful. And in all honesty, dyeing your hair will. Growing your hair will. Femininity and youth is biologically something that we’re, I think, programmed to look for.

LAURA STASSI

Yeah. So what if I kept it gray but grew it longer? You know, like Emmylou Harris.

MICHELLE JACOBY

You know what? You’re gonna be successful no matter what. I’m just telling you that you’ll have a larger dating pool of men to choose from if you decide to dye it brown, or whatever color you feel happy with.

LAURA STASSI

Okay, I think this is something that we definitely need to bring — we’re going to have a, like a Facebook poll.

MICHELLE JACOBY

And you know what, some people might be mad at me. And I just want to say, you’re beautiful the way you are. I’m just — my job is to tell you what’s going to give you the best odds of finding a partner. And I’ve been doing this for 13 years and in my experience, my advice is sound.

LAURA STASSI

Yes, no. Yeah.

MICHELLE JACOBY

But do what makes you feel beautiful, first and foremost. That’s the most important thing.

LAURA STASSI

And may we say that you are 56? Did you say …

MICHELLE JACOBY

Fifty-six.

LAURA STASSI

Fifty-six. And you have beautiful, naturally still, brown hair.

MICHELLE JACOBY

Yeah, I haven’t gone gray yet. But I will, I’m sure.

LAURA STASSI

I have — I think I told you I have — two of my four sisters, two of them are still very dark-haired. So, okay.

MICHELLE JACOBY

Thank you for the compliment. But you know what? You are gorgeous.

LAURA STASSI

Now I noticed that your husband has gray hair.

MICHELLE JACOBY

Yeah, he’s gray. He doesn’t like his gray hair. And that’s an interesting thing too, because you’ve heard the term gray fox, like some men. So I think it’s unfair. But I think some men as they age, they just become distinguished looking and more delicious as they get older.

LAURA STASSI

Yeah.

MICHELLE JACOBY

But I don’t as I’m getting older, feel more delicious on the outside. I feel more delicious on the inside. But you know, aging and changing physically, it’s — it has its moments. Sometimes it’s an adjustment, but I do think we get better on the inside as we age. He doesn’t like it. And I told him if he wants to use a shampoo or something to make it brown. I’m cool with it. But I think he looks super handsome.

LAURA STASSI

Yeah. I do too.

MICHELLE JACOBY

I just think we should do what makes us feel most comfortable. Having said that, though, for women, especially. But I’ve had male clients who’ve dyed their hair. I had a gentleman I was working with who was in his early 60s. And he wanted to date women who were a little bit younger. But their comments were always like, yeah, he feels too old for me, you know. And then he dyed his hair and it actually made his whole appearance seem more youthful, and he had more success. So, it is what it is.

LAURA STASSI

Thank you.

MICHELLE JACOBY

You’re welcome.

LAURA STASSI

I compared a photo of myself from 2018, when I had fake brown lowlights, with a recent one I took wearing the same dress. And I have to admit, Michelle may have a point — though I think my dye job helped me look younger than 58 whereas my natural gray hair makes me look my age – 61. Is there anything wrong with that? Plus, I’m remembering that my hair for the 2018 photo was freshly lowlighted, and even then I see some problem spots poking through. Anyone who’s ever dyed their hair knows that maintaining the facade takes a lot of time and money.

I firmly believe that we’re not getting older, we’re getting better. And even though Clairol came up with that line, I’d like to think it’s true — even if we ditch the dye.

 Episode transcripts are posted on the Dating While Gray website before they are thoroughly proofread. The audio of this episode is the authoritative record. For terms of use and permissions, please email laura@datingwhilegray.com.