Lakshmi Rengarajan Digs Deep for Midlife Daters

She's a midlife dating coach and podcaster with an unconventional take on how to "get back out there."

Hi Lakshmi, and welcome to the Womancake interview. How has your work day been going?

My work day has been great. Just a lot of switching contexts all the time, which seems to be part of the benefits and joy of work today, and they're totally different and require completely different parts of your brain and completely different temperaments. I don't think I'm the only one dealing with that.

I completely relate to what you're saying. I am literally switching hour by hour sometimes, during my workday. You’re a well-respected Dating Coach in a very crowded field, but you're doing something unique and original. I would love for you to talk about The Later Dater, and how you do it?

The Later Dater Today is the latest of my 15 years working in and around dating. I started out by doing storytelling singles events. Back in 2010 I went on to work at Match.com as their director of event design. I worked in marketing and building out programs there, and I have also hosted multiple podcasts on dating. But there's always been one aspect of it [that] I think is such a fascinating thing. I am a dating coach, but I'm also a dating culture researcher, and I think that's what makes me a great coach, because I've been doing it for so long.

Then a couple of years ago was when I really [started] to focus specifically on dating and midlife. I felt like dating in midlife had always been sort of overlooked, or it had a singular narrative, like the narrative around like divorce. There's so many different reasons why someone would be dating in midlife. Midlife itself is different, and I just didn't really feel like anyone was covering it, and I thought I was probably one of the best suited to cover it, because I've studied dating from so many different angles.

Dating apps have been around for a long tie now, but in the past few years many people have expressed a very high level of dissatisfaction with the current landscape. I'm curious, as a researcher, what do you see? What's interesting to you about it right now?

This is actually a very nuanced and interesting discussion, and there's a lot of different reasons for that. One is actually, I don't think the frustration has gotten worse. I just think you hear about it more. I think when people were [on] dating [apps] back then were a little bit more quiet about it. I think the big, historic watershed moment is when it went from desktop to mobile, when the [mobile] apps came on the scene. That's when all of these people [arrived] that had never dated online before. And now it was becoming the only way to date.

I think the volume of people just got bigger, so obviously the complaints got bigger, right? So for me, having done this for so long, the complaints aren't actually that different. It's just louder. Literally, people are saying the exact same things that people were complaining about ten or fifteen years ago.

So let's talk about midlife women in particular. What are some of the common frustrations that you see? Here I recognize my own bias, as I'm thinking about heterosexual women.

Just for consistency, let’s stick with heterosexual [daters]. I speak to everybody, but that is my expertise, and my identity.

If someone is coming on and they've been divorced, [which] peaks in the mid-40s, it's really just people thinking it's going to be easy, and that they know how to date, which is why I do what I do. Dating is actually a skill and an art form. Like a lot of skills and art forms at the basic level, it looks very obvious, like, “All I gotta do is sign up for a dating site, and then I'm gonna go on to dinner and I'll see if I like this person, and if they if they like me, we'll go out again.” But it's just not that simple. What a lot of people come up against is they don't know the world that they're entering, and it doesn't go as planned early on, and then they blame themselves.

[They don’t] understand the landscape, a lot of the psychology, a lot of the cultural shifts in dating. So a lot of times I'm just educating people about dating culture. Because like anything, if you don't understand the culture and you just sort of go somewhere, it's going to be jarring. It's going to feel like you're in the wrong place. So I think the thing that I see the most is just this, this misalignment of, “Well, I should know how to do this,” and then that not necessarily being the experience, and then people getting frustrated.

As regards the dating culture that you mentioned, what are some things that you think midlife women in particular should know?

One of the things is, I work a lot with people on how to talk about themselves. A lot of dating advice is about asking questions and kind of interviewing the other person. This is actually one of the worst things that you can do. [Interviewing] the person and find out what are they looking for, and blah, blah, blah. As I interview men a lot, [they tell me that] this just drains the energy from the conversation. I'm not blaming women at all. It's the advice that they're given. But what I really work with people on, among many other things, is in this context, in this modern dating culture, how can I really talk about myself in a way that is going to build emotional connection and tell the stories that I want to tell about who I am at this point in my life?

And that's actually not obvious. I deal with a lot of very successful, highly intelligent professional women who have amazing professional relationships, and because of that, don't realize that dating is an entirely different endeavor. So it's actually like, a very sweet, beautiful awakening, that while you might be an incredible mentor, an incredible friend, an incredible auntie, an incredible sister, dating is a different interaction. It's going to take a minute. I think one of the things with midlife women is they have so many reasons why they're just crushing life, and because of that, there might be some resistance to realizing, “Actually, I don't quite know how to do this!”

I think one of the things with midlife women is they have so many reasons why they're just crushing life, and because of that, there might be some resistance to realizing, “Actually, I don't quite know how to do this!”

Everything you're saying is familiar to me. By profession I'm an executive coach. I work with, I think, the same cohort of women that you're talking about. And it occurs to me, as you're speaking there, that I think part of the element that they're struggling with is vulnerability. What I hear from a lot of single women in that cohort, and single women who are my peers and my friends in my community, is that the psychological safety piece and the vulnerability piece is tricky for them to understand. I'm wondering, in your research, what role have you found that psychological safety plays, and what is the advice that you give women who are struggling with that in their dating life?

Interesting. I should say that that's not what I see. There's been so much [cultural] dialogue about vulnerability that women know the vulnerability thing. It's the one storytelling piece that they own, and they have actually over-indexed on vulnerability. They’re sort of trying to hotwire a connection by revealing things that maybe are not always the right idea on a first or second date. Just sort of like, in some cases, wanting to be vulnerable, coming in with that idea, but almost overshooting. We want to have the right amount of disclosure, that's the nuance and the challenge. [Often] women are all about quoting Brene Brown, like, “I need to be vulnerable.” So what I actually have to do is dial people back from that, and really work on telling the why, and the who, and how they've arrived at this point in their life. That's what they struggle with, telling an engaging and compelling story.

So would you say that women in that demographic are generally seeking marriage and long-term partnership? How does it break down?

That's something that sort of reveals itself as you spend time with people and you coach them, or you're doing research, is that the default setting is, “I should want marriage.” That’s kind of what people are conditioned to think they should be pursuing. It's just very hard-wired from your 20s and 30s, right? [But] is that ultimately what you want?

It may not be that. It may be a long distance relationship. It might be someone you just have dinner with once in a while, [or] someone you just have sex with. There's so many different relationship permutations that people don't really explore because we are so socialized to think of the long-term committed relationship as the ultimate relationship, and on the other end [of the spectrum] there's hooking up and one night stands. And there's this incredible fertile territory in the middle that is never really discussed in a very compassionate, productive way.

So a lot of what I'm doing with people is getting clear about that. Because most people come in, like, “I want to take dating seriously.” And actually, after doing some work, it's like, no, you actually don't want to take dating seriously. You want to bring a different energy to it, and you want to enjoy dating in a totally different way than how you were when you were younger. That is another outcome. It’s, “I want to get out there and date. I want to meet new people. I want to understand what I'm attracted to now, at 52, with everything that I have?” There's a blueprint that needs to be updated. Dating looks like something that's easy. I'm not saying it needs to be hard. I just think it's a lot more interesting and layered than people are given the space to explore.

There's so many different relationship permutations that people don't really explore because we are so socialized to think of the long-term committed relationship as the ultimate relationship, and on the other end [of the spectrum] there's hooking up and one night stands. And there's this incredible fertile territory in the middle that is never really discussed in a very compassionate, productive way.

What would you say to a midlife woman who is getting back into the dating pool after many years of being married, and is now divorced and single, and really wants to jump back in? Where should she start in this process that you're describing?

I would say number one is don't jump back in. Like, take a minute. One of the pieces of dating advice that's given to people a lot is like, “Just get back out there, just jump in.” I think it comes from a really good place, but it's mostly directed at midlife daters, right? People are like, “My son signed me up for a dating app.” But I think that if people just don't spend a little bit of time thinking about what they're getting into, understanding dating culture, understanding what they even want, understanding how they want to show up on a date, and I don't mean physically, I mean energetically, it's bound to be a shitty experience. And if you have a shitty experience, you are not going to be out there for very long.

That's my next question. I have a couple girlfriends who've been out there for so long that they're just exhausted and burned out, and they kind of don't know where to go from here. What would you say to them?

It's such a case-by-case situation, so I'm very cautious about talking in broad strokes, because it's your personal thing. But what I would say is a lot of women, and men, tend to show up on dates and kind of wait to feel something. I think that that is a mistake. I think you have to be very active, especially as a midlife theater, an active participant in dating. You're going to have to do the work. So when people have told me that they've been out there for a long time, some of my questions are, to what degree and what frequency? Like, have you been on the apps? Because people tend to do cycles, like, they'll do three weeks on, and then back off, and then they go on [again]. So to me it would be understanding the actual architecture of how long they were there, and what actually happened. People will be like, “Well, I went on so-and-so coffee dates,” like, they're checking boxes. I need to understand the fidelity of what being out there means, [in order to] guide them.

Thank you, that’s good to know. I'm going to pivot to some Womancake questions now. The theme of our entire magazine this year is, “Increasing Older Women's Visibility.” Will you share the environment in which you currently feel the most invisible, and the one where you feel the most visible, and why?

Most invisible [is] maybe like social media. I don't feel like my personality translates to that place. I love meeting people in person. I don't have an issue with Zoom, but I have not figured out how to talk to an inanimate object and feel like I'm connecting [to a person through the screen.]

I feel really visible right now with my best friend. She has two young children, and she has made such an incredible effort to weave me into her life, as busy as she is.

Female friendships are so important. Do you have any daily wellness habits or practices that are meaningful?

I exercise six days a week. The way that I approach exercise now is so different from how it was younger, like, I'm not doing big cardio workouts, I'm doing a lot of joint work and stretching. I love a good skincare routine. I'm willing to try anything and everything. And then I'm just really big on, especially for my clients, and especially for dating, showing up with energy that would make the other person's day better.

Nice, I try to bring that attitude to my clients as well. What is your favorite guilty pleasure treat?

The dark chocolate peanut butter cups from Trader Joe's.

Do you have a favorite power song that we can add to our Power Songs Playlist?

Right now I’m totally vibing to Chappell Roan. Like, obsessed. “Red Wine Supernova.”

Great, I’ll add it. How does wisdom manifest through you at this stage of your life?

I feel like the way that I talk about dating is coming from someone who has watched it in so many different chapters. And I mean, no shade to anybody else, but I just see so many dating coaches come on the scene, and they've decided that they're going to be a dating coach or something. The fact that I've seen so many chapters to dating [and] had a front row seat to it, when I'm working with clients, I don't feel like I'm giving advice. I'm actually helping them pull out their own wisdom. Instead of [them asking], “What do you think I should do?” or, “Which app should I be on? Is this a good picture of me?” We don't operate at that level. We go a level deeper.

What is an aspect of your character that you've grown to love, and one that you still struggle with?

I'm super opinionated about dating, and I have to dial it back sometimes, because it's a fun topic that people want to talk about. I actually think it is fun, but it's so serious, too. It's serious in the sense that it's such a big part of people's lives, and it's not, I think, given the gravitas and the humor that it deserves. And so sometimes, when I'm talking about dating, I think that I can be off-putting sometimes to people unless they really hear what I'm saying. So it's a good thing and a bad thing. It makes me an incredible coach and probably kind of annoying sometimes, if you meet me on a train or something.

Will you share anything about your perimenopause or menopause experience that you think would be helpful to a woman who's going through it?

I have really found cinnamon to be great for hot flashes and stuff. One of my friends is a doctor, and I was with her last weekend, and I was telling her, “Hey, I don't want to sound like a weirdo, but, I've been taking cinnamon.” And she was like, “That makes total sense, because that means it's connected to your blood sugar, that it’s a blood sugar response.” I just get these pills from CVS, like capsules, and I take two of them. It’s like [hot flashes] are nonexistent if I take them. I was taking them every day, and I just kind of tapered, and now I just have them once in a while, but literally, it's not an issue anymore.

Will you share a book, movie, podcast or TV show that you're currently enjoying?

I think Trevor Noah has the best podcast right now. I love seeing him go from humorist to social critic. I just think that he and Christiana and Josh, his co-hosts, are having my favorite conversations about the world right now.

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This interview has been edited for length and clarity.

You can find Lakshmi on her podcast, her website, and on LinkedIn.