Amelia Diamond: Tell me how you met.
Elaine Welteroth: So how did we meet, Jonathan?
Jonathan Singletary: No, you go first this time.
Elaine: We met when we were twelve or thirteen. We’re from the Bay area, we grew up in the same church, our moms were in the same choir, we were in the same youth choir at some point and then I just realized —
Jonathan: You were in the choir?
Elaine: For like two seconds.
Jonathan: Two seconds, okay.
Amelia: Were you guys in the same grade?
Elaine: Yeah, essentially. He’s a year younger than me in school but —
Jonathan: I’m six months younger than her.
Elaine: He’s a child.
Jonathan: We’re the same age.
Elaine: He’s one grade lower than me, though.
Amelia: That was a big deal in high school!
Jonathan: It was a little bit of a big deal.
Elaine: He wore really big glasses. Like really big glasses.
Jonathan: She always says that but can’t find the pictures of them. They’re really not that big.
Elaine: He definitely wore really big glasses, they took up half of his face and —
Jonathan: That’s not true.
Elaine: He had this amazing smile. I remember thinking, “He’s going to be a really great husband to some lucky lady one day.”
Amelia: Do you remember meeting Elaine?
Jonathan: I don’t remember meeting her — I remember seeing her and being like, “Oh, she’s bad.” It’s funny, I feel like every guy from our church at that time remembers Elaine.
My sister’s always like, “I don’t really know if I remember her from church.” But as a twelve- or thirteen-year-old guy it’s like, yeah, you noticed her.
Elaine: This is the most he’s ever given. I’m always like, “You totally had a crush on me!” And he’s like, “No, I really didn’t.” I’m like, “You were in love with me from the first time you met me,” and he’s like, “No, I thought you were cute.” Cute?
Jonathan: We literally never spoke outside of church until three or four years ago in New York.
Elaine: I would come home during Christmas break and so would he. We went to different colleges and would see one another. I remember this one time, I came home with my New York boyfriend and Jonathan came up to me, acting like the guy was not standing there.
Jonathan: He acted like he wasn’t standing there. I don’t remember — was he standing there?
Elaine: You made an effort. I was at the front of the church and you were somewhere else and you navigated your way through people to come over and be like “hey” and flash your pretty little smile and I was like, “Oh my gosh, Jonathan. Little Jonathan, you’re growing up!” There was just something nice about that interaction. I don’t remember any detail other than that thought: he’s a good guy, he’s going to go places and make some girl real happy one day.
Jonathan: She was smiling at me. When I think back to those conversations, I feel like we were always just like smiling at each other. We were permanently smiling at each other through the whole thing, and then her guy was somewhere in the background.
Elaine: He faded into the background.
Jonathan: That interaction was kind of it. I was in grad school in a PhD program but I was looking to get into the pharmaceutical industry. That was my plan at the time: get my PhD, and then I’ll go and be a consultant at McKinsey, and then do some pharmaceutical consulting. Three or four years later, I realized, “I don’t want to do this anymore.” I was really bored by science at that depth, was passionate about music and didn’t want to be in a lab, so I went to a startup. The startup was acquired by Google, and then I was at Google for a year and a half.
My end goal was marketing within the music industry. While I was at Google I had my eye on New York because I felt that it was where everything was happening in music. I had an opportunity to interview at a few places including Shazam, a Google job in New York and this new label. I reached out to Elaine to tell her I was coming to visit New York. That was in 2013. I hit her on Facebook.
Elaine: So he hits me on Facebook and weirdly, I got it (I never check my Facebook messages) but once I saw that one, I realized he had hit me before and I just didn’t see them.
He’s like, “Hey, I’m coming to New York for some interviews, would love to meet up for drinks if you have some time and if not no worries, just know I’m proud of you.” Something like that. And then he’s like, “Best, Jonathan.” I was like, why not, I’ll meet up with this guy from church.
In my mind it was absolutely innocent. I remember him as the nice guy from church. It was definitely a friend-zone thing in my mind. But when he arrived I was like, “Where did these shoulders come from?” He looked like such a man. And I don’t know, I just loved the way he articulated his thoughts. I was just like, I like you as a person.
We laughed at all the same things. Had so much to talk about. Also, he wasn’t checking for me. You can feel that energy when someone’s trying to make it a date — he wasn’t doing that at all, there was no motive. It was like the best hang-out session. We were supposed to just do drinks but ended up doing dinner and went some place else for dessert. We went to three places.
Then he’s like, “I told some friends I’d meet up with them, do you mind if they come here?” His friends show up and I know one of them and then they were planning to go to the party that I was going to go to, so we went together.
Jonathan: I was only there for four days to interview. That week had been such a buzz for me — I was having really awesome meetings with industry folks who I never thought I’d have the opportunity to meet, and this was in the middle of that. My brain was in focus mode. It was just good, real. There was no scheming going on.
Elaine: We were supposed to connect the year before —
Jonathan: Oh, Governors Ball.
Elaine: But it never happened. I was trying to find him, and we never found each other.
Jonathan: Both of our phones died but we were there at the same time.
Amelia: It’s all about timing.
Jonathan: Yeah, it wasn’t supposed to happen then, apparently.
Elaine: I remember that at the end of the New York night, I was low-key feeling the kid. When we were walking to the cab, I was like, “What are you doing this weekend?” And he’s like, “I’m going to D.C. My girl’s out there.” And I was like, “Girl?”
In my head I was like, “I’m sorry, what?” But I played it off like, “Oh cool, cool, cool.” I don’t talk to anyone with a girlfriend, so the thought process immediately changed.
Jonathan: I don’t even remember that moment. I was in an on-again, off-again five-year relationship from senior year of college. It was long distance. I was in California, she was in D.C. We had broken up for a year before that and we had just started talking again after being broken up. I was like, alright, I’m coming to the East Coast, maybe we can make it work. And if I’m going to try, I’m going to be laser-focused on this relationship and not at all have wandering eyes. That’s where I was in my relationship at the time. I think I had blinders up to the chemistry that we had, even though it was a good time. There wasn’t space for it.
Elaine: That was in December, right after my birthday. He ended up moving to New York in February and we didn’t speak until March.
Jonathan: In between that time, it was becoming clear that my relationship wasn’t going to work. We were going through the, “Can we save it?” phase and I was like, “I don’t think we can.”
Elaine: My mom’s birthday is March 10th. She came out for her birthday to visit and we ended up doing this big dinner at my apartment. I invited a bunch of people over and my mom and I cooked for everyone. It was a warm family affair, and I invited Jonathan — totally as a friend. He had a girlfriend. I invited other guys and friends, you know.
Jonathan has a very different recollection of this, which is funny, because it kind of switched. My feeling on the first date — which wasn’t a date — was very much, “There’s something going on here. This is so exciting,” but he wasn’t thinking of me in a romantic context at all. So at this dinner, he was in the friend zone.
Jonathan: She’s like, “He’s the guy with a girlfriend,” and I’m like, “I’m the guy with the ending relationship.”
Elaine: But I didn’t know that.
Jonathan: I also think there’s this other element that I can’t fully explain, but when you see somebody like Elaine on Facebook or in pictures with big hair and celebrities, she’s a little intimidating. I probably had thoughts of, “She’s out of my league.”
Elaine: You’ve never said that either! You are just giving the goods today. Keep going.
Jonathan: The first time we sat down and met it was really casual. This time, when I walked in, my relationship was on the way out. There was something about seeing her with her mom and friends and hosting, just being in her own space, I had never seen her like that.
I just remember looking at her as she entertained her friends. I remember thinking, “I really like this person a lot.” Something deep was there.
That night was really fun, really good. We hugged at the end of the night–
Elaine: Which I don’t even remember.
Jonathan: A really special hug. She lingered super long. She texted me later and was like, “Thank you for coming, it wouldn’t have been the same without you!” And that’s when I was like, “She loves me!”
Elaine: Which is so funny because I think I said that to everyone. Because it truly wouldn’t have been the same!
Jonathan: At that moment I was like, okay, I want to hang out with her again. I was telling myself that she was just a friend from back home. That night I was like, “We’ve got to hang out, it’s been too long and I’ve been here for a month. What are you doing this week? We should grab a drink.”
Elaine: And then the plotting began.
Jonathan: It wasn’t plotting. Later that week I was in her area for happy hour with coworkers and she was having drinks with friends, so we met up.
Elaine: There is this guy at the restaurant with me and my friends who I wasn’t into, but he was trying it. Jonathan arrives and it’s this breath of fresh air. It’s instantly good vibes. It’s just like, my person has arrived, thank god, you’re saving me, this is now fun.
Jonathan: You can tell when a guy is scanning the situation like, “Who’s this dude? This is supposed to be my time,” so I was like, okay, I’ll give him his space.
Elaine: I liked Jonathan so much that I was trying to hook him up with my friend that night. Then later, when everyone was going home, we split into two cabs: uptown and downtown. Jonathan and I were both going uptown so we split a cab. We both lived in Harlem at the time.
I was not trying to go home with that other guy, who was in the downtown cab.
Jonathan and I get in the car and we have this long ride to Harlem. I spent the entire time talking about this confusing situation I was in with another guy. I was like, “What do you think, do you think he likes me, what does this mean?” The way I saw it, Jonathan was going to be my new straight guy friend who could offer dating advice. Meanwhile, Jonathan did not apply for that position.
Jonathan: But I had a girlfriend, so I had to play the friend role on principle.
Elaine: He kept smiling and I really wasn’t picking up on it. I was so consumed with this conundrum I was in that I truly would’ve asked a puppy what he thought, so I wasn’t as aware as I normally am. At one point Jonathan was just like, “Yeah, I don’t know what’s wrong with this dude. If I were him, I would’ve wifed you already.” And I was like…
Jonathan: It was just this long story about this dude who had an opportunity to be in a relationship with her but it just seemed like he was being weak about it. If I were in his shoes it would’ve been a done deal. So yeah, I said that.
Elaine: And when he said that I was like, wait a minute…is he feeling it? And am I ruining this right now? But — I guess because I got nervous — I kept talking.
Jonathan: Finally I was like, “I can’t do this. I can’t be the guy who you talk to about other guys, especially when I’m kind of feeling you.” And that was the turning point. I think I kind of reached my threshold of how much of the conversation about another dude I could handle and I was like, alright, I feel like I’m being fake right now.
Elaine: When he said that I was like, “I’m feeling you, too” or, “I can’t say that I’m not,” or something like that. What did I say?
Jonathan: Your reaction was a mix between —
Elaine: I was conflicted.
Jonathan: Flattered or happy, excited and also —
Elaine: Hella conflicted. In the same sentence that I said, “I’m feeling you, too,” or some confirmatory response, I also said, “but I’m a girl’s girl and I don’t do that. You are technically still together with someone.”
Jonathan: We established the fact that this was obviously not going anywhere.
That next day, I knew I really enjoyed this person. But I was feeling guilty. I had gone through this whole thing the year before where I re-examined my entire life. I wanted all of my relationships to be about full transparency and honesty. A big prayer of mine was how to love people better in my relationships, and a big part of that meant being honest and respecting the person you are with enough to tell them the hard, difficult truth.
I told my girlfriend that I was having feelings for someone else. She deserved to have all of the information.
Then Elaine and I got coffee. I told her my girlfriend and I talked, and that I needed space to figure out my relationship.
Elaine: He was so upfront and so respectful given the situation we were in. I really respected how he handled it. We agreed it was best to not talk, and we didn’t for over a month.
It was clear to me that he had decided before we met what kind of value system he had and everything he does is going to bounce off that. It was very clean-cut for him, how he handled everything.
We did go to church after that coffee, though. And the whole sermon was about letting go in the name of your future.
Jonathan: I was in there like, God, don’t allow me to manipulate this sermon into something that I want to hear. But the message was literally, “There’s a new season.”
Elaine: Jonathan, the girl sitting next to you is your future. Let go of your past. Like for real. And then at some point they were like, “Rise to your feet and hold the hand of your neighbor.” So we join hands and it felt like…it just…you know when there is so much energy in the handhold, the first handhold?
After church he walked me to the train. And we said goodbye.
Jonathan: I went to D.C. shortly after. We broke up while I was there.
Elaine: It had been a month, a month and a half. We hadn’t talked. Then one day I woke up and really missed Jonathan. I missed my friend. So I asked my roommate if I should call him.
Then I answered my own question: “No, I’m not going to call him. I’m going to honor what we have.”
He hits me up that same day. We met for sushi and he tells me that they broke up. Then he and I caught up and the next day I left for L.A. I remember thinking, “He’s a great guy, but he just got out of a serious relationship. He is fresh to New York. He needs to like, do the New York single thing.” So when I came back, we set all of these rules: We can hang out, but like it’s not like that.
Jonathan: She kept saying that, but I was not interested in doing the New York thing. I don’t like going out. I don’t. She didn’t believe that.
Elaine: I was still processing my thing that had ended six months prior. So we hung out, but I felt he needed time and I needed time. I decided I needed to be alone for a while. I cut my hair off, changed jobs, moved. I said that this was going to be my Carrie Bradshaw moment. I just wanted to date and write about it and experience single life in New York, which I hadn’t done before. I felt like I kept default falling into relationships, and I didn’t want this thing with Jonathan to be that.
I signed up for a half marathon and said I would be busy training for it. But Jonathan was like, “Cool, I’ll run with you on the treadmill.”
Jonathan: We really just wanted to hang out with each other. So we did.
Elaine: So we did. Then one night he was running with me. We ran five miles on the treadmill in my gym. Afterwards, we went up to my apartment for him to grab his stuff, and on his way out, we kissed.
Jonathan: After like, a month of hanging out.
Elaine: It sounds so cheesy that I don’t even want to describe it, but it was…it was the best. It was the best kiss ever.
Jonathan: There was magic in it. It was kind of a trip.
Elaine: Yeah, it was a trip. It’s like not that big of a deal, to kiss, but for us it was something special. I remember that when my race day came, you came out to Brooklyn and brought me oranges and bananas and water and Gatorade.
Jonathan: And that was kind of it. From there…
Amelia: It was just on after the marathon?
Elaine: Yeah, it was just on after the marathon. The first time that we were ever out like, publicly together, was at this day party that turned into a night party, and a few guys who I had been dating previously were there. At some point Jonathan asked me, “So are you my girl?”
Jonathan: It just kind of was. It didn’t need the conversation, but we had it anyway at some point.
Elaine: So then flash forward.
Jonathan: Two and a half years later. Through that time I left my tech job and decided to pursue music full time. I moved to L.A. for six months to do this. That was a huge challenge for a relationship, especially for her, because it’s like, wait you don’t have a stable job now? You’re just gonna figure it out and be a musician?
I’ve been writing songs since I was like 11. I grew up playing piano. I had a lot of little random performances, like opening up for Bruno Mars in Vegas. There were all of these signals that music was what I was supposed to be doing, but I would ignore them. I thought I had to take a traditional path. Finally I was like, if I don’t do this now, I’m going to regret not giving this a real go. So the last year and a half, two years ago, has been full music.
That’s been one of our biggest challenges. But it also helped me be able to be a better partner, I think. Just growing in security and identity and deeper into my purpose and really my relationship with god has helped us in a lot of ways.
Elaine: Yeah, it was a challenge. My dad is a musician and my brother is a musician and I’ve always sought out the exact opposite. I wanted different from what I saw growing up. Jonathan came in this package that was very different from my dad in every way possible — and then mixed it all up. There are realities to the musician’s lifestyle that I am exposed to that Jonathan is not.
Jonathan represented stability to me. When that started to change, it was really challenging. I struggled with it. But it made me have to question and set up what my value system is going to be. And I always said I want to be happy. I always said that I want to be with someone who is a good person at their core and that is the most important thing to me. And I’ve never met anyone who is a better person than Jonathan. I’ve never met anyone who is kinder than Jonathan, as supportive or loving as Jonathan. So it was like how could I possibly judge him for like wanting to pursue his passion when I had the opportunity to do that, too?
I had to become a better person and put my fear aside.
Jonathan: We had so many honest, hard conversations. There was a period of time where I was like, it might just be easier if I go away, do my thing and come back when I’ve got it all figured out. Men want to be perfect before we commit to somebody. But there is no such thing as perfect — that’s what I learned from other married people. It is way more valuable to grow with somebody.
We got engaged this December.
Amelia: I know! Congratulations!
Elaine: He lied to me for a week. I was home for Christmas and he told me he was in Florida. We’d talk on the phone and I’d be like, “How’s the weather, babe?”
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. I almost had a panic attack.
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. His parents were there. His parents came out of the corner. His dad had like three video cameras stashed in the room. And then I looked and there was a laptop in front of me on top of the TV with a Google hangout — all of our closest friends were on the Google Hangout, watching the whole thing.
I was dying. I was truly dying. Dead. I think I died that night.
Jonathan: It was only a month ago. What’s the date today?
Elaine: It might be today, the 23rd. You know, we almost broke up during that time he was in L.A., when we were going through that transition. It was really hard, but we worked through it. At some point, what felt like a choice — to be in or out of the relationship — went away. There is no choice: You’re my person and we’re in it so let’s make the best of it and let’s talk through it and let’s do this. That surrendering was a big part of what led us to able to get engaged. Like I’m not going —
Jonathan: To do this without you.
Elaine: I just don’t want to do this without you.
Follow Elaine and Teen Vogue on Instagram @elainewelteroth, @teenvogue. Visit Jonathan’s website and follow him on Instagram @jonathansingletary and check out his SoundCloud. Photos by Krista Anna Lewis.