Now What.

Now What.

Ask Me Anything

Inside date night with me, Max, and of course Timmy

Sep 24, 2025
∙ Paid

You learn a lot about a person in four years.

That’s how long I’ve been with my partner, Max. In that time, I’ve discovered a lot. Like how he loves anything combining chocolate with peanut butter. Or that he cannot carry a tune. And that if I kiss the back of his head, he will always make a purring sound. I’m sure he could name similar things about me. But what we rarely take the time to figure out is the deeper stuff. These kinds of questions are especially difficult when you’ve spent the past five months thousands of miles apart.

This Sunday will be our anniversary, and we will once again not be in the same place. So, we celebrated a little early. A couple weeks ago, I played hooky from work to bar crawl through our favorite Manhattan spots. We also spent time asking each other questions. With the understanding that I could share the answers with my lovely readers.

What follows will tell you a lot about our relationship. Namely, that I’m the funny one. But also: how we’d like to challenge ourselves in the next year, the closest we’ve come to breaking up, and whether Max truly has a favorite Timmy. All of it may surprise you.

Max: I’ll start with one that shouldn’t be too difficult. Pick one habit—emphasis on one—that you’d want me to change.

Rachel: Chewing with your mouth open. You smack your lips, and it drives me nuts.

That’s fair.

Was there a moment that you remember knowing you were in love with me?

I don’t know if there is a singular moment, but I have distinct memories of you leaving me cards when I lived in Tribeca. You never left that apartment without leaving a card or chocolate or something. No one had ever really done that for me.

I have a similar question. We’ve been together four years, which is kind of crazy. What is the moment where you truly believed this relationship could work?

There have been a few moments where I’ve had that feeling and then doubted myself. But a turning point for me—and this is such an odd answer—is when we got food poisoning in San Francisco. Because I thought if we could see each other throwing up our guts, covered in poop, and still want to be together, then that’s true love.

It took a while for me to have faith in us. I’m highly skeptical.

Clearly.

What is something about your life since meeting me that’s changed for the better?

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