15 Couples on Falling and Staying in Love

It's kind of a funny story: Elaine Welteroth and Jonathan Singletary discuss how they met.

If you think about it too much, falling in love seems so weird right? If love stories are to be believed, it often boils down to two things: 1. some strange, undefinable feeling and 2. being ready. WHAT IS THAT? Two people have to feel the same thing at the same time and at the right time in their two separate lives and then it just…works? I need Bill Nye to explain it to me with Twitter science.

While I largely consider myself a cynic, I genuinely enjoy hearing people talk about how they fell and how they stay in love. I think it has something to do with hoping that there are people out there who experience the private act of love in the same way I do. In honor of Feel Good Month, I’ve rounded up a few of the juiciest tidbits, best advice and most awwwwww-inducing moments from Man Repeller’s It’s Kind of a Funny Story series. Please read through and then add your own. I’ll be here all day.

Elaine and Jonathan

How Elaine Welteroth and Her Fiancé Managed to Escape the Friend Zone

Jonathan: Her family had a Christmas party planned at her uncle’s in Napa, so I prepared this whole video with family photos and a video of her first birthday. There was footage of me driving up to her parents’ place, coming out with flowers to ask them permission to marry their daughter.

Elaine: But pause. Meanwhile, I’m two hours late. My uncle told me to be there at 3, I rolled up at 5. My little cousin, my niece, was like, “Come on Elaine, we are going to watch a home video.” So I was like, cool, home videos. Which I started Instagramming.

Jonathan: Because she’s Elaine, so like.

Elaine: My niece keeps trying to take the phone out of my hand. I’m like no, this is great content. Then our song started playing, but I didn’t think anything of it because it’s a song everyone loves.

Amelia: What’s your song?

Elaine: “Magic” by Coldplay. Everyone likes that song. So I thought, maybe this is just a song that they decided to put on. This is fine. Then everyone goes quiet. I look up. Our song is playing louder and I’m with my whole family: my uncle, my nieces, nephew, my dad, my brother, his girlfriend, uncles, aunts — everyone is there, and he comes around the corner in a suit, singing the song.

There was literally this moment where I was ejected from reality. I was a bystander watching it happen. It was not happening to me. I forgot that I had to engage.

Jonathan: I was on my knee like, “I need an answer here.”

Elaine: And I was like, “Of course, of course!” It was so emotional.

Melissa and Ron Silver

Melissa: “[T]here was a certain kind of unnamable feeling that I had that it would be right. That we would be good together.”

Amy and Frank

 It’s Kind of A Funny Story: Tibi’s Amy and Frank Smilovic

Amy: Make sure you know who you are, and even if you know who you are, make sure you know you can be someone else five or ten years from now. Your best friend travels with you through that journey, but someone else may not. I can’t even imagine who I was at 24. I had just moved from Georgia without a passport. So for us to have gone on this journey together, I feel like I’ve had so many different personalities on that ride. Make sure you’re with someone who’s comfortable to level with change.

Frank: It all starts with something that Amy’s dad told me when — actually, I think it was at our rehearsal dinner. He said, “Frank, just remember, it’s a roller coaster.” When you think about it, it’s a great analogy because I don’t like roller coasters — I get sick — but that’s what life is, and you need someone to be next to you when you’re throwing up. But also, someone who will celebrate with you when there is reason to celebrate.

Amy: Who do you want sitting next to you in that roller coaster?

Eva and Bobby

On Dating a Chef in New York

Haley: Do you remember saying “I love you” for the first time?

Eva: I do. I said it first, but I remember you said it with your eyes first.

Rajni and David

It’s Kind of a Funny Story: Rajni Jacques and David Dowd 

RajniWe met in college, at Rutgers. We had a class near one another and we would pass each other twice a week in the hallway, and he would stare at me.

David: Well, we had a weird thing. We would smile at one another.

Rajni: Well no, you were staring first and then I would smile.

David: This went on for months. Is that an exaggeration?

Rajni: Not an exaggeration. It was probably for two months.

David: We would just smile and stare.


David: I will say…going back to the beginning of this story, back to seeing you in the hallway and that weird smiling thing…I’ve never had that weird smiling thing with anyone else. It was like some crazy weird attraction that I hadn’t ever had before.

Simon and Jonathan

It’s Kind of a Funny Story: Simon Doonan and Jonathan Adler

Simon: We have something a lot of people don’t have: a great creative, humorous, physical rapport. We laugh at the same things, we both love me…(laughs)…no, we love each other. We are very, very lucky people. Some soldier on in their relationships and make compromises, but we didn’t have to do that. And we encourage each other. I did my column for the Observer for ten years, and he encouraged me so much. I would never have done that without him. Then I encourage him, because if you have a great relationship, you take risks and put yourself out there in a way you don’t when you’re on your own.

Taylor and Sam

A Love Story in Progress from a Regular New York Couple

Sam: There’s a lot of balance. With Taylor, I’m very confident about how I feel about her. Most other relationships have been fear-driven in some way or another. With Taylor, it’s just not fear-driven at all.

Paul and Siddhartha

It’s Kind of a Funny Story: Paul Andrew & Siddhartha Shukla

Paul: That was sort of the draw for me to you. You were wearing a perforated green Gucci jacket, which I think I fell in love with before I fell in love with you.

Lisa and Marlon

It’s Kind of a Funny Story: Lisa Salzer and Marlon Taylor-Wiles

Leandra: What about you, Lisa? When did you know?

Lisa: It was when we made eye contact downstairs. I really saw a big sparkle in his eyes. I felt that his soul seemed very nice — he seemed like a nice person, even from that one moment.

Céline and Colin

A Love Story I Need Everyone to Read Immediately

Colin: So the three of us were having dinner. And over the period of an hour, my friend saw us fall in love.

Amelia: What?

Colin: I swear to god. It was all chemical. We were both very aware that we had just fallen in love during this hour and a half.

Céline: After dinner, we all went back to the studio and had a private party until three in the morning. We played records and danced. And we felt so in love.

Then the next day, I was so scared. I was like, “What if it was just last night? It must have been the food.” But there was more and more attraction.

Then a couple of days later, after work, Colin told me, “I am in love with you.”

I told him, “Me too, I think. I’m scared.”

Hannah and Brendan

It’s Kind of a Funny Story: Hannah Bronfman and Brendan Fallis

Hannah:  I don’t remember what happened that night either but I remember we ended up going back to the Fontainebleau. I remember we were sitting on the steps and you were about to say goodbye to me and we sat down, and we were both like we don’t want this night to end. Let’s go to the beach. And we both fell asleep. I fell asleep in his arms.

Jan and Derek

It’s Kind of a Funny Story: Derek Lam and Jan-Hendrik Schlottmann

Jan: Finding someone is a different thing, though. Finding is something I can’t explain. My mother, I tell you, my mother’s story is funny because she was a widow for like 20 years, and she fell in love at 75 going to the opera with a guy her age.

Derek: He was just sitting next to her.

Jan: He had two tickets and he was alone, so he sold one ticket to her, and they have been together for four years now. You know, when you don’t look at all, it just happens. You just have to be aware and have the ability to see it. 

Matt and Irene

Irene Chen and Matthew Grenby of Parker Thatch

Matt: Life’s hard. What I love most about Irene is how she’s able to look at it with a sense of humor. Whatever we’re going through, to be able to both laugh at it and take a step back, even when in the middle of it, that’s very important. You don’t find that in a lot of people. I love all of the usual things, obviously, but that’s at the core of it.

Irene: For me it’s all of that. That sense of humor, and our shared aesthetic, but I also always know he’ll take care of me.

Matt: That’s the other thing. We can depend on each other.

Irene: It’s true, he’s just a solid man. He’s going to take care of us. Things could blow up, but we have each other. Building on what we have done is so important.

Matt: We count on each other.

Sachin & Babi

Sachin: If you’re looking for love, look for it for the right reasons. I’ve known people — friends of ours — where things have not worked out and I’ve always sort of questioned it. Were you in it for the right reasons? We got into it for the right reasons: we liked each other, we were great friends, we had common interests. There was no grand plan in my mind or I don’t think her mind either. It just kind of happened.

Kaelen and Simon

Kaelen and Simon Haworth

Kaelen: Did you see Best in Show? That part where she’s like, “We can talk, or not talk, for hours….we both like soup.” That’s this.

Photos by Krista Anna Lewis and Edith Young.

Nora Taylor

Nora Taylor

Nora Taylor is the Editor of Clever. She can frequently be found knocking things over in the greater New York City area.

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