Two Good to be True

A bad second date can be a deal breaker for a budding relationship. But it’s not often that a good one gives someone cold feet. 

That’s what happened with this week’s Love Letter featured couple. Caroline and Haden met in college, but didn’t start dating until after Haden had graduated. A great first date led to a second, but the second was too good. 

At the time, Caroline was a little disillusioned with the dating scene, and the prospect of becoming infatuated with someone after recently experiencing heartbreak wasn’t the most appealing prospect. She told Haden that it would probably be best if they cut things off. 

Haden understood where she was coming from, but convinced her to give him one more shot. Ten years later, they spoke to Meet Cutes NYC while their first child slept. 

Here’s their story.

How did you meet?

Caroline: We met at Shenandoah conservatory, which is a music conservatory school attached to Shenandoah University in Winchester, Virginia. I was a freshman and Haden was a junior at the time that we met. 

Playwrights was something that happened every Thursday night. Afterwards, people would hang out or go to iHOP or something like that. I had gone to a theater high school, so I hadn’t dated a lot because there was kind of slim pickings. I was ready to date and see who was out there. 

I remember the exact moment that I met Hayden, we were standing outside of Playwrights and I was actually interested in a guy in his friend group at the time and I was kind of scoping things out. 

But I remember very distinctly him saying “Hi, I’m Haden.” 

From that point on, I dated a few people long distance from back home. I remember that every day for an entire semester, we would pass each other on this bridge that connected the university to the conservatory. And apparently I’d say really corny things to him like “nice helmet” or “safety first” when I saw him on his bike. We were friendly acquaintances.

What was your first impression of Caroline? 

Haden: I don’t remember anything else about that evening. I don't remember the plays that we saw, I don't remember who else was really there. I just remember meeting her there. I thought she was so beautiful and funny and interesting. But the timing was never really right those first couple of years.

How did you end up getting together?

Haden: I graduated, but I was still playing in a band that was headquartered in Winchester. So I was commuting back and forth basically every week. 

I was recording some music with my bandmates, and during a break we were just kind of talking about relationships and stuff. And we went on Facebook while we were talking about people, and Caroline’s name came up. 

It just seemed like the right time. I didn’t have her phone number or any way to get in contact with her, so I sent her a message and asked her to get coffee.

Do you remember getting that message?

Caroline: I remember it so distinctly. I was pretty over dating by that point, especially being long distance and me putting in a lot more effort into people than they were putting into me. I had decided to book a trip to LA for spring break to see one of my best friends and clear my head. 

We were getting pizza and this message from Haden pops up. My initial reaction was just I can’t do this. I am so over dating people. But my friend said to me “Caroline, you’re overthinking this. He asked you to coffee, he didn’t ask you to get married.” So I said “Sure, I’ll get coffee with you.”

How did your first date go?

Caroline: After we got coffee, we extended the date. It was free Rita’s day, so we got free ice cream. I was 21, he was 22. We were both looking for companionship, we weren’t trying to get married. It was very clear for the both us very soon in that it we clicked.

I remember what sealed the deal for a second date is I have this kind of obscure favorite movie, What About Bob with Bill Murray. And he knew this movie when I told him, and I was like “No way! Nobody ever knows this movie.” 

I think we actually watched it on our second date. And that night I started to get really freaked out because I was coming from a place of heartbreak and loss to this intense feeling of I really like this person. So I actually tried to end things on the second date.

You tried to end things? How’d you change her mind?

Haden: I could understand where she was coming from, but at the same time I knew that maybe it was a little misguided. So I just tried to keep her talking until she gave me one more chance to go out again the next week.

Did you pull out all the stops?

Haden: I tried to. That was the goal. I had recently gotten one of those instant cameras, so I had that. And I knew she liked sunflowers, so I went and bought her some of those. I surprised her at her apartment, and we went to the park and we walked around and took photos. It was kind of rainy, but it was still a fun day.

What do you think brought you two together after years of being acquaintances?

Caroline: I think there are a lot of options and distractions. I think there's something to be said for paying attention to energy, to how someone makes you feel when you're with them, or when you're communicating with them and like, allowing love to grow. Because I think you could miss out on a lot of that. That was always there, but we didn't really know what was there until we explored that.

Haden: I would say you never really know where something’s gonna go. I mean, I always liked her, but I thought “Oh, she’s just just a nice girl I knew at school.” There’s a ton of people in my life who are just like that, but I only ended up with her. 

🤔 Poll

📊 Last Week We Asked…

• [poll] “What's the key to a successful dating profile?”

  • 40% said “Authenticity”

  • 24% said “A touch of humor”

  • 0% said “Professional photos”

  • 36% said “A mix of all of the above”

And a meet-cuter shared:

• “I feel authenticity should “rule the runway” with this because “a mix of all the above”, although probably the best answer for an exam, isn’t the truest representation. Authenticity I feel, is.”

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Interviewed and transcribed by Nicolas Vega. This interview has been edited for length and clarity.