I’ve been digging through San Diego Magazine’s archives recently, working to understand what dating has looked like over the past 76 years of the mag’s existence. As I browsed, I came across an article in the February 2016 issue featuring a byline I recognized: Kai Oliver-Kurtin.
The SD local has been a contributor to the mag for nearly 10 years and still writes for us today. The six-page spread, entitled “Great Dates,” includes everything from a directory of places to take your love to fully planned romantic itineraries and a quiz to complete with your partner when neither of you can decide what to do on your night out.
It also features Oliver-Kurtin’s thoughts on dating in the city as a 31-year-old. Here’s what she had to say:
Flaky, that’s how I would describe the dating scene here. In recent memory, I’ve had at least four guys cancel on me the day of, or the hour before, our planned date. It’s frustrating. There are just so many options at people’s fingertips with all the dating apps (Tinder, Bumble, Hinge, OkCupid, Match, Coffee Meets Bagel—yes, I’ve tried them all at different times), and if you’re never met in person, guys are less inclined to care about wasting your time or hurting your feelings. I would much prefer to meet someone while I’m out and about, or through mutual friends.
But dating apps have made people lazy. Men don’t have to approach you at a bar and risk rejection, because they’ve got hundreds of other options. They can send a massage to 25 women that says something like, “Sup? Cute smile” and actually begin a conversation while hiding behind their phones. Chances are, at least one of those women will respond as long as he’s employed and over 5-foot-10. (The topic of height as it relates to online dating could be an entirely separate article—so could the blatant disregard for grammar. It sux.)
I’m 31. I don’t go to PB to meet guys. But if I were 21, I probably would. The Gaslamp can be hit or miss. It’s better if you go to a lounge, restaurant bar, or dive bar so that you can actually have a conversation. Downtown clubs are for bottle service, EDM (electronic dance music), and one-night stands. Today, thirtysomethings are flocking to places like Kettner Exchange in Little Italy that feel more mature than the Gaslamp. The trendy neighborhood is becoming more of a late-night destination than ever before—remember when people had romantic dates at charming Italian restaurants there? Alas, this is the world we live in now. So keep calm and swipe on.
Naturally, I was curious about how her love life has fared in the past eight years. Did it ever get any better or easier? I caught up with Oliver-Kurtin this week to hear what it’s been like since that time (hint: she’s now married with two kids) and what advice she’d offer to singles today.
How did you end up sharing your perspective about San Diego dating in the magazine?
The editors back then were putting together the big love issue for February. And they were like, “We have all these couples and dating ideas for couples. But what about what the singles are doing?”
So, they reached out. I must have been feeling some kind of way, because I unleashed on my friend who was an editor there. I thought it was just an email between the two of us. I was like, “Oh my God, these guys are awful. And I hate dating.” I was so negative. But they went with it.
When I came home and got the print copy out of my mailbox, I was like, “Oh my God, there’s my email.”
You’re married now. How long was it after that piece that you met your now-husband?
We met in 2017 at the Kaaboo Del Mar music festival. We had a mutual friend. I got separated [from my friends], and then suddenly his group of guy friends [called me over]. My husband actually went to college with [my friend] in Illinois, so I ended up hanging out with him for the three-day festival. And at the end of it, I was like, “Oh, I’m never going to see this guy again. He lives in LA; he’s just my festival fling.”
He was like, “Why don’t you come up to LA? I’ll show you around the city.” I ended up going up there and we’ve been together ever since.
What was your dating history before meeting him?
I really hadn’t dated too much and I hadn’t really had many long-term relationships at all. I was really sour on dating apps. I just really didn’t want to do the online thing, and I think part of that maybe was because I’m a writer and I wanted a story with it. I didn’t want online to be my story, which is so silly because that’s most people’s story that I meet these days. But at the time, it mattered to me. I really wanted to meet someone organically, but most of my friends are older than me and most of them were already married and didn’t really know many single people.
When you started dating your husband, what stood out to you that was different from the guys you had met previously?
Whenever I talk to my mom about this, she’s like, “I remember the first time you called me after meeting him. And the words you used to describe him were: ‘He was really kind and he was really smart.’”
We had a really good time together. It was interesting meeting within a music festival environment because we both had had few drinks and were kind of loose and open. We were getting to know each other without sitting across from each other at a dinner table interviewing each other.
It was very organic. It felt like there was no pressure, and we just really had fun together. I think that’s really the biggest part. I felt like when I was going into dates, it was like, “I must see if this is going to be a future partner.”
I felt like it was more serious. And with [him], it was like, “I’m just kind of hanging out with this guy, and this probably isn’t even going anywhere.” So there was no pressure.
What were some ways that you determined that your values and the things that really mattered to you aligned?
He’s Indian American. He was born and raised in Chicago and is a first-generation American, so there are cultural differences. But he was super open and honest about that, and no topics were off limits.
He was also willing to jump right into my world. I used to bring him to media events, even though he’s more of an introvert, and I was like, “Let’s see how he does at this wine festival.” And, you know, he would always surprise me and rise to the occasion and pull out this extroverted self.
I think just kind of seeing him in my world, seeing him with my friends and family, and then having deeper conversations—I felt like we just really made good use of our limited time together.
What did you learn about yourself while dating that you had to adjust or work on in order to make the relationship work?
I usually like to over-schedule myself. I’m one of those people who’s like, “I’m going to pack 75 things into this one day,” and he is horrified by that. If we’re on vacation, he’s like, “Well, this isn’t a vacation if you’ve planned 100 things today.” So I’m learning, like, “Okay, I need to do what’s going to work for us.”
I’d also been single for so long that I really only had to only consider myself and my needs and what works for me. I needed someone who could stand up to me and who would kind of put me in my place if I needed [that], and not someone who’s going to let me steamroll them. And he is that; he will totally call me on my BS.
What are some of your single friends saying about dating in San Diego nowadays?
We had a friend over the other night, and she was saying, “I’ve taken the pressure off myself and now I’m just dating for the experiences.” Instead of going into every date like, “Is this going to last forever?” She’s like, “I’m trying to have fun and go to restaurants that I want to try or do activities that I want to try.” Again, taking that pressure off. I like that perspective.
What advice would you give others as they try to date?
I’ve realized, at least between me and my husband, that when we’re trying to have serious conversations, one of the best places to have them is in the car because they can’t bolt and you’re stuck there. But you don’t have to look at them, so if it’s really uncomfortable, you can just keep looking straight forward. Or going on walks together. We walk a lot together, and when we need to talk through hard stuff, it’s like, “Okay, let’s go walk it out.”
I feel like it makes it less intense, less pressured, and we can come in and out of conversation. We can take a long pause and come back to it after thinking through things. He’s more analytical than I am, so [often] he needs the time and space to think through how he’s feeling about something.
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