Zibby Owens: Holly Martyn is the author of Would It Kill You to Put on Some Lipstick? She’s a writer, storyteller, memoirist, mother, frequent flyer, and former Wall Street executive who shares her many adventures in life, travel, and dating.

Welcome, Holly. Thanks for coming on “Moms Don’t Have Time to Read Books.”

Holly Martyn: Thanks for having me on, Zibby.

Zibby: We spoke about a month ago on my Instagram Live show, which was much fun. I loved talking to you then. I wanted to hear more from you now, so that’s how we got here.

Holly: I know where our conversation kind of lit up the last time we spoke was when — you’re a divorced mom as well. Now you’ve remarried. We had started to get into some of the psychological aspects of being a single mom and being divorced and dating, which I think you could relate to as well.

Zibby: Yeah. You want to talk about that? That sounds juicy and good.

Holly: I think part of what you have to do when you are deciding to get divorced or going through that process and dating is to kind of get your head on straight. One of the things that I realized as I was writing the book was that I felt this huge sense of shame about being divorced. I felt like in many ways our society reinforces that view of women, particularly single women and single moms. Would you agree with that?

Zibby: You know, I think just sometimes people don’t know what to do with things that don’t fit in all the right boxes, necessarily. I think when you go from the world of being part of a couple to then not, particularly the people who were still part of couples don’t exactly know how to handle it. I think they immediately feel badly for you when maybe you don’t need any sympathy. People make a lot of assumptions about what you must feel or you must think. I think some people, and I don’t know if you experienced this, didn’t know how to, I know at least when I got separated and then divorced, didn’t exactly know how to deal with me or talk to me or what it meant for them. I think that’s the other thing. When a close friend or something gets divorced, and I don’t know if this happened with your friends, people are like, if it could happen to her, it could happen to me, or I better stay away, like it’s contagious or something.

Holly: Yeah, divorce cooties.

Zibby: Exactly. Back up for two seconds and tell everybody the name of your book, why you wrote your book, what’s in your book. Then let’s go back to this.

Holly: The name of my book is Would It Kill You to Put on Some Lipstick?: A Year and 100 Dates. It’s a memoir/manual about the first year after my divorce as I grappled with being a single mom and having to date again. I was absolutely flabbergasted that I was twice divorced. I thought I’d never have to date again. Frankly, I’d never really dated that much ever. I decided to chronicle the experience of trying to rebuild my life.

Zibby: How’d it go?

Holly: I think we talked about this last time. The backstory was that I had been sitting in a spa feeling sorry for myself. I happened upon an article about a woman in a position similar to mine. She was a widow in her late thirties with a newborn. Her husband had died of cancer. She crossed paths with the late Joan Rivers who knew the woman well enough to look at her and say, “You’re kind of letting yourself go. Would it kill you to put on some lipstick? Set up an online account. Go on a hundred dates. You’ll meet somebody.” I was struck by that. I thought, wow, could it really be that simple? That’s the motivation and the idea behind my memoir. I found that the book got away from me in the best of ways. It’s a little bit like Sex and the City meets Eat Pray Love. I talk about a lot of the funny dates, the heartbreak, and then also what’s happening with me in my head and my heart as I try to reconcile my life up until this point. That became a big thing that I was looking at as I was dating again. I really didn’t want to make the same mistakes I’d made in the past. I wanted a fresh start. I thought, this is really my chance to get it right this time.

Zibby: I always make proclamations like that. This time, I’m not going to snap at my kids. This new year, now I’m going to be patient. I’m going to not repeat the same things that have been my default coping. Somehow, they keep creeping back in. Did you find that happened to you?

Holly: One thing I did do well is that I decided to keep an open mind. What I found was that because I’d already had a child, I’d had my attempt at a happy traditional family, I thought, this time around, rather than dating and maybe being with someone, marrying somebody that I “should” be with, what if I just cleared the decks and kept an open mind about age, income, all of those things, just being totally openminded and openhearted to who I might date and to not be bound by societal ideas of what I should be doing?

Zibby: That sounds like something you can achieve.

Holly: What is great is that what was different this time around for me when I was dating is dating apps and online dating didn’t exist the last time I was single. Suddenly, the dating landscape had changed. It really opens up opportunities for you to meet people that you would’ve never crossed paths with otherwise. In the past, we tended to date and marry the people we worked with or the people we went to school with or the people that we met at church or synagogue, people in our circle. Technology allows us now to really break right out of that. It’s exciting.

Zibby: How did your daughter handle your hundred dates?

Holly: At the time, she was eight, nine years old. She was a hilarious peanut gallery. I don’t know if you saw my book trailer, but there’s a moment in the book trailer which literally happened exactly as in real life. I thought, I’m going to update my wardrobe. I’m going to try to be a little more chic. I’m going to get out of my mom garb. I go out and I buy this big fluffy jacket and get on some cool jeans. I’m getting ready to go out on a date. I walk out. I say to my daughter, “How do I look?” She looks me up and down head to toe and says, “You look like a werewolf.” She was always correcting me. I’d come out and she’d go, “Don’t you think you need a camisole under that?” I tried to be really honest with her about the things that were going through my head. I wanted her to start to think about, who should we be with? Who shouldn’t we be with? Why? I would only introduce her to somebody if I had become serious about the person. Even if she hadn’t met the person, she would say, “How’s it going with X, Y, Z?” I would give her a cleaned-up version for a child, but explain, “I broke up with him because he treated me this way,” or “It’s going well because…” I wanted her to learn. It was something that I was never taught. How do we be treated well in love?

Zibby: Yes, it’s so important. The whole thing of dating when you have kids is such a crazy experience. I remember when I was already in a relationship with Kyle, who became my husband, I was about to introduce them. I remember asking the kids, “If you could design a perfect guy for me to date, what characteristics would be important to you?” I remember holding my breath thinking, I hope they pick some of the things that he has.

Holly: Did they?

Zibby: They did. He’s a pretty great guy. I was lucky, but I was sort of holding my breath there. I think that one of them said that he had to play with dolls. I had a little kid too. He didn’t meet all of the boxes, but the ones that he could meet that were reasonable. At least, I wanted them to know, not that they could pick who I ended up with, but that their input really mattered to me because it was a decision that was going to be for all of us and not just something that would benefit or affect me. They were integral players in the whole thing.

Holly: It’s a new member of the family. It’s a big deal.

Zibby: It’s like adopting a grown-up.

Holly: Exactly, and their family and maybe their kids. Did Kyle bring children as well?

Zibby: He did not. No, he’s just been a great stepdad to my four kids. I told him, “I’m not having more kids, so you should just run the other way and go marry some young, pretty thing who wants to have her own family. You should just do that.” He’s like, “No, I want to be with you.” He probably regrets it.

Holly: I’m sure he does not.

Zibby: Obviously, that would add a layer of complication to things. No, we didn’t have to deal with that. Going back to your book, having gone on all these dates and realized, perhaps, what’s more important to you and what’s not as important to you, going forward, what are some of the most important things you learned? What are some of the things that if somebody else was like, “Gosh, where do I even start in this process? I’m totally overwhelmed,” what would your advice be for that person or all of that?

Holly: I would say the first thing is to ask yourself if you’re really serious about wanting to have love in your life again. Some people approach it halfheartedly and say, yeah, maybe. Or maybe they’re not really being honest with themselves. For me, I realized I did want to find my person. I did want love in my life. I was willing to commit to it. I wasn’t going to do this in a half-assed way. I was going to go for it. The whole premise of the book kind of set me up to do that. It gave me the discipline. I started to approach dating in my forties with a plan and a commitment. I told myself that whenever my daughter was with her dad I would not stay at home and Netflix and eat pizza. I would go down to the local wine bar or go into the city to a restaurant and eat dinner up at the bar. If someone spoke to me or started a conversation, I would talk to people. I would start to expand my circle.

That opened up a whole new world. It opened up a whole new world for me not only in terms of people that I might date. I made great women friends. I’ve made great professional contacts. That’s one thing that happens to people when they get divorced. You kind of lose some of your friends. You lose some family members. People tend to take sides. It’s really important when you get divorced to expand your circle. Expand your circle with fresh, positive people who are going to support you in this new phase of your life. It’s an opportunity. It’s painful, but it’s also an opportunity to do some spring cleaning. Then the other thing I did to get the dates was I did go on dating apps and try different apps. I got some dates that way. I met some wonderful people that way. Then the third thing that I did was I put the world out to friends and family. Hey, I’m single. If you know of anybody who’s single and you want to set me up on a blind date, I’ll go on it. I was really openminded about it. I figured it’s one hour out of your life to go have a coffee or go have a drink. Again, I met wonderful people that way too.

Zibby: Can you share where you ended up in relationship land?

Holly: It’s funny. I wrote Would It Kill You to Put on Some Lipstick? about four or five years ago. It covered a year of my life. I don’t want to give away the ending, but let’s just say the formula worked. I did meet somebody really wonderful. Since then, he and I are not together, but remain good friends. Our daughters remain good friends. Not too long after that, I ended up being in a two-year relationship with somebody who set me up on a blind date. He and I are not together anymore. We’re still actually very close friends. I can’t say that I’ve regretted anybody I’ve dated or any relationship I’ve been in. I think the further I get into dating, the more I realize that I every combination of two human beings, it’s like new chemicals. It’s always new and fresh. Just when you think that you’ve seen it all, met every personality type, you just never know what’s around the corner. It’s really exciting. I’m dating. I have a few stalkers. Of course, I haven’t really been able to see anybody very much in this pandemic.

Zibby: I love what you just said about every new interaction between two people creates new chemicals or whatever because it’s so true. I feel like in every relationship, it’s not just you learning about them. A new piece of you kind of rises up to meet them as well, a new version of yourself. You can snap into it so quickly, not dramatically different, but just a slightly different version. Does that make sense?

Holly: Absolutely. I read something today on Instagram. Someone had a quote about just how dating can trigger us, positively or negatively, into parts of ourselves, parts of our childhood that we may not even know is there. Whether we can face those triggers and those feelings, both positive and negative — then this is also happening in the person you’ve met — can also determine whether you choose to stay in that relationship. In some cases, it spurs you to bolt, right?

Zibby: Totally. I also realized — I try to give advice to friends who are dating about this. I used to say, what was wrong with this guy? I don’t know. I would highlight something about him. I didn’t like his shirt. I didn’t like the way he folded up his sleeves. I didn’t like that he wore a necklace. I don’t know, something stupid. But it wasn’t that at all. It’s just sometimes it’s so hard to put a finger on when you don’t know why, but it just wasn’t right. It’s so much easier to say this particular external thing is what did it when that has nothing to do with it.

Holly: It’s hard to come up with a shorthand for friends or even acquaintances of, “Oh, you’re not with so-and-so anymore? What happened?”

Zibby: Right, that too.

Holly: What’s the sound bite to get them off your case?

Zibby: Relationships are so multilayered. There’s so much that goes into every relationship, dating, marriage, our ex-husbands. It’s so impossible to sum up any of it. What happened with your ten-year — no, there’s no one answer. It was a lifetime of something.

Holly: I write about this in Lipstick as well. My relationship with my ex-husband, the father of my daughter, has completely changed. We are truly friends. He has a girlfriend he’s been with for six or seven years now. We get along great. It wasn’t that in the beginning. We were all just, I don’t want to say enemies, but there was no trust. We had to build a new relationship and a new extended family for our girl that we love.

Zibby: I think time is so critical. Things change so much over time after divorce, even with the friends. I don’t know if you found this with your friends. Some people who I felt like at the very beginning were vocal opponents or did things that really hurt my feelings right at the beginning have since, now that it’s been five years or so, come around and said, “You know what? I regretted my behavior. I’m really sorry for that.” I feel like time in divorce, and probably in everything, it just changes so much for you and the people around you and also your relationship afterwards. Time itself just changes so much.

Holly: It’s just what we were talking about a minute ago. When one couple splits up, it often motivates your circle to look at their own marriages and their own relationships. Sometimes what you’re hearing in terms of their feedback about your split-up is really more about what’s going on with them than what’s going on with you.

Zibby: Yes. I wish I had known that the day that I was going around telling everybody. Some people would burst into tears. Some people would be like, “How do you feel?” Some people would just be like, “How could that happen?” It’s a lot. You have to take on everyone else’s stuff.

Holly: Yeah, at a time when you’re feeling, chances are, pretty depleted.

Zibby: Yeah, probably. I don’t know. Anyway, your book, so how long did it take, the actual writing of the book? Did you like it enough that you would want to do another book? If so, what would that be? If not, what’s next?

Holly: It took a year to live it. Then it took about another three years to write it. I literally have ten different incarnations of the book. The tenth was the one that went to press. What’s exciting, what’s happening in the last few months, and I can’t give too much detail, but I’ve actually been approached to turn it into a television series.

Zibby: That’s awesome. I’m so happy for you.

Holly: Thank you. We’re moving along. It would be sort of like a divorced Sex and the City. There is this episodic nature to a hundred dates. I’m definitely interested in being a writer on that project. I would definitely commit myself to that. I don’t see myself as someone who’s going to spend the rest of her life writing about her love life. I’ve started my next book which is called Drinking with Mimes. It’s stories of me back in the day when we could still do this, jump on an airplane, show up in a new country, unscripted by myself and write about the people that I meet on the road, the stories, the crazy adventures. That book has been going really well. I think it’s a great sequel, but not only to show that just because you get divorced and even if you haven’t found somebody yet, you can still have these great adventures, and I did. The first trip I did, I went to Punta Mita, Mexico. Then I went to Copenhagen for Christmas. By the way, randomly met Katy Perry at the time when she was there.

Zibby: Oh, my gosh. That’s a good title, by the way, Copenhagen for Christmas.

Holly: Yeah. Then I got a bonus trip at Christmas. A friend of mine who’s a writer said, “You got to go over to Sweden and meet my brother. He’s a mime.” That’s why it’s called Drinking with Mimes. He’s a literal mime, you know, the people that don’t speak. You’re with me?

Zibby: I’m with you. I’m following you.

Holly: Then from there, I went to Lisbon for New Year’s and ended up meeting this fabulous gay man who owned a small palace and invited me to his New Year’s party.

Zibby: Why not?

Holly: Why not? That was the start of the book. Once we get out of this COVID situation and I’m able to travel again, I want to finish off that book.

Zibby: Excellent. Do you have any advice to aspiring authors?

Holly: The only advice I have is don’t give up and just keep at it. I literally got up at five o’clock in the morning for fourteen years before I got published. Just dig in and don’t give up. The writer that I thought I was at year one and what my voice was then bears almost no resemblance to what I write now. It’s a process that you just have to go through. There’s no shortcuts. Enjoy that process. If you enjoy the process, then whether you’re published or not really becomes irrelevant.

Zibby: Very true. Awesome. Holly, thank you. I feel like I had a little mini-therapy session of my own here about all the stuff that happened five years ago. Thank you for sharing your experiences and your great book and all the rest. Thank you.

Holly: Thank you so much. Take good care.

Zibby: You too. Bye.

Holly: Bye, Zibby.