Dating post-Divorce with Jennifer Tracy – Episode 63

The Recap

Jennifer goes solo in this very special episode as she talks all things dating. Jennifer shows incredible vulnerability opening up about her separation and subsequent divorce from her husband. She recounts her experiences with dating apps and the “interesting” people she met. Jennifer speaks to the value she places on intimacy and investing the time to truly get to know someone on an intimate level. Jennifer shares her story of falling in love with someone recently and the heartbreak that followed when things ended between them. Finally, Jennifer explains why she has ditched the dating apps completely and shares her plans to focus her energy on more productive areas of her life.

Episode Highlights

02:12 – Jennifer recaps her summer

03:15 – Jennifer announces this month’s charity initiative, Amnesty International

05:36 – Jennifer thanks her entire podcast team for their work

07:02 – Jennifer thanks her newest sponsor, Flirty Girl Guide

09:31 – Introducing today’s topic, dating

10:36 – Jennifer opens up about her separation and divorce from her husband

11:20 – Dating apps

15:22 – The value Jennifer places on intimacy

17:27 – Vulnerability

18:52 – Why Jennifer shut off dating apps for good

20:37 – Jennifer gets vulnerable about meeting someone and falling in love recently

23:06 – Dealing with the aftermath of heartbreak

26:06 – Putting energy towards more productive things than swiping left and right

27:41 – Jennifer recalls the time she acted as a dominatrix for a guy she met

29:29 – Jennifer reminds the audience to use their 10% discount at Flirty Girl Guide

Tweetable Quotes

Links Mentioned

Jennifer’s Charity for September – https://www.amnesty.org

 Flirty Girl Guide Website – https://www.flirtygirlguide.com/ (Use the code ‘MILF10’ for a 10% discount)

Connect with Jennifer

MILF Podcast

JenniferTracy.com

Jennifer on Instagram

Jennifer on Twitter

Jennifer on Facebook

Jennifer on Linkedin

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Transcript

Read Full Transcript

Jennifer Tracy: They want to jump past the vulnerability that happens when you slowly open yourself to somebody. I mean slowly, that could be in a two and three hour date one night or it could be over two or three months or two or three years or two or three decades. For me, that's what turns me on, vulnerability, like real vulnerability, not forced vulnerability, but just someone being honest and opening up about who they are and their life experience. It's why I have a podcast. It's why I'm a writer. It's why I work with writers, because I am fascinated by that. I'm turned on by it. I think it's so profoundly beautiful. For me, that's what I'm going for. You just can't leap into that when you're texting someone on an app. You don't even know their last name or where they grew up or what their childhood was like or what their first time having sex was like. Those are the things that make us up as people.
Speaker 2: You're listening to the MILF Podcast. This is the show where we talk about motherhood and sexuality with amazing women with fascinating stories to share on the joys of being MILF. Now, here's your host, the MILF-iest MILF I know, Jennifer Tracy.
Jennifer Tracy: Hey, guys. Welcome back to the show. This is MILF Podcast, the show where we talk about motherhood, entrepreneurship, sexuality, and everything in between. I am Jennifer Tracy, your host. Welcome. It is September. Summer is officially over, which is many things. It's a little sad. It's also exciting. There's a fresh crispness, not Christmas yet. I'm not rushing you. There's a fresh crispness in the air even though here in Los Angeles, September, October, and now November, thank you, global warming, are the hottest of months of the year, but most places there's a cool crisp breeze, and the leaves are starting to change maybe or thinking about changing. There's something really cool about that. I always loved the fall. I still love the fall even though I have to wait until December to get it here in LA, but I'm not complaining, maybe a little bit.
Jennifer Tracy: Yeah. I had an amazing summer. I got to travel with my son. We went to Hawaii on a vacation, just the two of us. It was magical. It was his first time being there since he was five months old, so he didn't really remember it, but he really discovered for the first time the magic of the island and the water there. There's a quality there that is unlike any other place that I've been. That was really fun to watch and the bonding that happened between us and the things that we were able to talk about that we don't have the time or the space or that it just doesn't flow in a natural way when we're in our normal routine even when it's summertime. There's something wonderful about traveling that I forget because I don't usually take time to do it, but we did, and I'm so glad we did. I learned new things about him, and I think he learned new things about me. It was really, really, really lovely. I'm so grateful I was able to have that time.
Jennifer Tracy: Now school's back in session, and here we are. This month's give, so for September I chose Amnesty International because the Dynasty Typewriter was doing this thing where they were promoting Amnesty International. If you made a donation, you got like a little fun sign on the marquee, and so I did that, not for the marquee because I was already on the marquee before when I had my live show there at the beautiful Dynasty Typewriter, such an amazing theater. You should go check out their shows if you're here in LA. They have an amazing roster of comedians and improv shows and live podcasts. It's a beautiful space. Anyway, the great thing about that was that it turned me back onto Amnesty International. I knew who they were. I knew of them, but I didn't really know how they operated.
Jennifer Tracy: When I went to their website to make my donation, I learned so much more. Their website is Amnesty.org. One of the many things that's really cool about this organization is they have been around for a long time, and they have so many roots in so many different places because they're fighting for human rights, I mean, all over the world. They have roots and teams and actionable things happening in every country in the world. You can choose a country to donate to if there's something that is important to you there. You can choose a cause to donate to. You can donate for women's rights. You can donate to protect activists in countries where they're not allowed to speak their voice. They don't have free speech. You can donate for free speech. Check it out.
Jennifer Tracy: I always encourage just people to really look at what's out there if you can't make a difference yourself by going. Especially when you're a mom of a small child, you can't really drop everything and go to South Africa or the Faroe Islands or Ethiopia and work for a month. I mean, I guess you could. I'm sure people do that have small children, but it's really difficult. If you can donate money to someone who can dedicate that time, then at least it's, for me, it just feels like I'm doing something, as much or as little as you can. Every dollar counts. Check them out, Amnesty.org. I'm going to get a little more involved with them, and so I'll be sharing kind of what I'm learning along the way. With that, I also just want to give thanks to my MILF Podcast team because I can't do this alone.
Jennifer Tracy: I'm just grateful to my wonderful producer, Sarah, who really holds this whole thing together for me and keeps me on track, reminds me like, "Hey, you need to do this," always very gently. Sarah, I love you so much. Our amazing editor, Derek; my show notes writer, Kevin; Liz, who keeps everything running on time and is just always so impeccable. I really appreciate you, Liz. Corrine and the other Sarah on the other side of the country, who help me get my message out and get my courses together for my writing courses and help me promote my brand so that people know who I am and what I'm doing and how I'm trying to elevate women's voices and women's stories. That's how many people it takes, guys. At least for me, at least for this broad, that's how many people it takes. There's always more adding every day.
Jennifer Tracy: Oh, and Sky. Sky just came onboard, and we love Sky. She's so beautiful and amazing. She just helps me keep my life organized and keep all these different pieces of the puzzle organized. I do that not only to publicly thank them because they deserve that, but I also do it to let you guys know that I don't do this by myself. It looks the way it looks because I have a team of people that help me do it. That's a perfect lead in to thank our sponsor for this week's show, Flirty Girl Guide. Flirty Girl Guide is my friend Brooke Christian. Brooke Christian was on the show in episode 23. She is delightful. She's become a really close friend I'm so honored to say. Flirty Girl Guide is a curated website. Well, she's a lot of things. She does a blog. She just launched her new podcast called Sexy as a Mother, which I will be a guest on. I'm so excited. We recorded our episode a couple weeks ago.
Jennifer Tracy: When you go on the site, so it's FlirtyGirlGuide.com, she has all these beautiful curated kits of sex toys. Now, what's so great about Brooke and her messaging is she's a mom. She's saying to women, married, not married, kids, no kids, but especially those of us that are moms, it's harder to find that time, for me. I'll speak for myself and many of the women that I've interviewed have said so on the show. It's really hard to find not only the time for sex but just the desire. It's in there. It's still in there, but it's really hard to get in touch with it. It's hard to find it with your partner when you've been together for a long time or it's easy to get complacent in that area. Obviously, she has all these really fun curated kits on here, and she has couples' toys.
Jennifer Tracy: She has a couple of my favorite vibrators on here. One is the Lelo, the Womanizer that I just discovered through a friend, and my other vibrator is a Lelo. She has 50 Shades of Gray the pinch nipple clamps. I mean, why not? Different lubricants, which we all know we need to have the good lubricants, not the crappy ones. Yeah, check her out. Also, for my MILF listeners, she has been so generous and given everyone who listens to my show a 10% discount with the exclusive code MILF10. When you go to make your purchase, just use the discount code MILF10, and you'll get 10% off everything. Thank you, Flirty Girl Guide, and keep your eyes out for Sexy as a Mother, the podcast. Go listen and keep your eyes out for my episode. I'm really excited. We had a really saucy talk in my office. She came out to LA, and we got to do it, the podcast, not have sex, but you never know. You never know.
Jennifer Tracy: Guys, this week, it's just me. It's just me on the show. I don't have a guest on the show. What do you think about that? How do you feel? Well, let me tell you what I'm going to be talking about. I'm going to be talking about something that I really don't talk about that often, and yet I have been asked many times... I'm going to take a sip of water because my mouth just got dry, I think because I'm nervous. I've been asked to talk about this many times, and I'm just, "I don't know. I'm not ready. That's really, really personal," but I'm ready, and I'm going to talk about dating. I'm going to talk about dating as a single woman in her mid-40s, which I am all, a single mom I mean, its challenges and the hilarity of it and the loneliness of it and the swipe app generation and how, you know, that's really challenging to just dive into as an older person who didn't kind of grow up with smartphones.
Jennifer Tracy: Here I go. I have been separated since December of 2016. We separated, and then our divorce was final this last October, 2018. It took a minute, but, you know, after we were separated about I think three months in, my husband said, "I want to take monogamy off the table," and I said, "Okay." I knew that that meant that he was wanting to date women, and I just sort of sat with that for a while, which is fine. I mean, we were separated, and that's what he wanted, and I respected that. Then, several months later, I want to say it was August of 2017, I decided to try the app thing on the urgings of several girl friends and one of my guy friends, who is gay, and he was on the apps and having success meeting men. I said, "Okay. Okay. Okay. I'll do it," so I did it.
Jennifer Tracy: The long short of that was I was only on it for, I don't know, maybe three months. I went on a lot of dates with a lot of really young guys. I didn't know I needed to set the age thing, so I kept getting all these like 25-year-olds wanting to take me out. I thought, "Let me just try that. I don't know. Why not? That seems kind of MILF-y." They were all sweet, like every person that I met, and every person that I have met in person has been very kind and sweet and just wasn't a match from the apps. I found that like, at the time I was 42. I guess I was 42, 41, 42. I guess, yeah. No, I was 42. You know, these guys were 25, 26, 27. It was difficult to find, at least with those pairings. I know many people that are married, happily married, with people that are 20 years younger than they are. They have lots to talk about.
Jennifer Tracy: I mean, it really just depends on the pairing, but these boys that I was going out with, a lot of them were just wanting to talk about college or what their new job was because that was the maximum experience that they had so far. I remember that. I remember being that age and talking about college and high school. That's your experience level at that point. I got off the apps. I had a couple of crazy experiences on the apps. One guy just texting on the app wanted me to fuck his dog. I don't think he wanted me to come over and fuck his dog, but he kept saying, like sexting me about the dog and what the dog would be doing to me. I wish I'd kept it. I wish I'd kept it because I would read it to you guys. I said, "Wait. Am I petting the dog?" He's like, "No, the dog is doing this."
Jennifer Tracy: I'm like, "Whoa, whoa, whoa. No, no, no. I'm not into that. I'm into sex with human beings," and I remember he said, "Oh, come on. It's my fantasy. Just go with it." I just was like, "Okay. Delete," because, there again, I was even giving him the benefit of the doubt, saying, "Oh, no. Let me clarify for you. Let me clarify what I'm into," even though it was clear he didn't give a shit what I was into. I find that that is common, not always, but it does happen a lot with these online things because the anonymity allows people to act in a certain way that they probably wouldn't act, I mean, very most likely would not act in person or on a phone call. They can be very, deviant isn't the right word, but just their dirtiest selves, which isn't a bad thing, but, again, I was talking with someone yesterday about how... Because I just went on the apps again.
Jennifer Tracy: I'm going to fast forward. I just went on again 12 days ago, and I just deleted it after 12 days of it because I had a date last night that went awry, which I will share some pieces of it with you. What happens more often I think, in my experience and in many of my girl friends' experiences who are on these apps, is that there's this leap that people want to take. I'm saying people because I don't feel like it's fair to say that it's just men even though I'm only dealing with men. That's what I'm dating, cis gender men. There's this leap that people want to take. They want to skip all of the groundwork that, in my opinion, is paramount to building any kind of intimacy or real intimacy. I guess people can have meaningless sex, and that's totally okay. It's totally okay.
Jennifer Tracy: As long as you're being safe and protecting your body, and you're not hurting anybody else, go for it. Have as much sex as you want. I think that that is great. It's liberating. It's not for me. It's never been for me. It doesn't feel good for me. It doesn't satiate anything for me, but I absolutely I support anyone in doing what they need to do that feels good in their body and their sexuality and expressing that as long as it's not harming themselves or someone else. That's everything, like literally everything. I made a joke in my opening monologue for my live show a couple weeks ago about how one of these young guys that I had dated, that's how I learned what ass play was. Not that I didn't know about anal sex, not that I didn't know about pegging, not that I didn't know about those things, but I had never heard it called ass play, and I didn't know that many young millennial men currently are into having their ass played with.
Jennifer Tracy: That's fine. That's totally healthy and fine. The anus is full of amazing nerves that make sex incredible. I get that. I'm not opposed to that. The thing that I was talking about in that monologue is that this young man kind of put that on the table when we really didn't know each other at all. For me, it was almost like, "I like orange juice." I just felt like it was just the wrong time and the wrong place to bring it up. There wasn't an intimate moment even happening, intimate emotionally, intimate intellectually. It was just sort of this thing that he kind of lobbed out on the table that I thought, "Wait, what?" I didn't even know what it was. I had to ask him to clarify what he meant.
Jennifer Tracy: I think there's this thing that happens where people want to just jump past all of the vulnerability, because that's really what it is, because that's really fucking scary. They want to jump past the vulnerability that happens when you slowly open yourself to somebody. I mean slowly, that could be in a two and three hour date one night or it could be over two or three months or two or three years or two or three decades. For me, that's what turns me on, vulnerability, like real vulnerability, not forced vulnerability, but just someone being honest and opening up about who they are and their life experiences. It's why I have a podcast. It's why I'm a writer. It's why I work with writers, because I am fascinated by that. I'm turned on by it. I think it's so profoundly beautiful. For me, that's what I'm going for. You just can't leap into that when you're texting someone on an app.
Jennifer Tracy: You don't even know their last name or where they grew up or what their childhood was like or what their first time having sex was like. Those are the things that make us up as people just as much as my son's vacation with me to Maui is now a part of the fabric of his being, that he had those experiences, that he laughed at something that someone did in the ocean next to him when they... You know what I mean? That some girl popped up out of the pool and her top was off, and he saw her breasts and thought that was just crazy and hilarious. Oh my god. He couldn't stop giggling about it. He'll always remember that. Anyway, I'm digressing, but I think that... For me, ultimately, that's why I shut off the app again this time, was because I felt like... I will get to the date.
Jennifer Tracy: You guys will get some of the details. I just felt like I was swiping left. Swiping left on the app that I was on... There's so many apps. Oh my god. There's so many apps. There's Tinder. There's Hinge. There's Raya. There's the one I was on a couple years ago was called The League. There's Bumble, of course. There's, I mean, I don't even know. There's a new one every day. Coffee Meets Bagel? I don't know. It's a lot. That's, I think, how everyone would say to me, "That's how people meet." I was like, "Is it? I mean, it is. It is a way, but it's not the only way." I just didn't want to have to keep looking through all of these. It made me sad. It made me lonely looking at all of these men who had posted their things on there.
Jennifer Tracy: Some of them were hiding behind either no profile picture or, you know, a totally self-deprecating bio that said, one said, "I'm a piece of shit. You probably shouldn't date me." It was this really cute person. I just thought, "Why would you put that? Do you think that's funny? I guess you think that's funny. I don't know." Outlandish photos. I thought of this live show that I actually want to do called Swipe Wrong, where we have just the most outlandish ones, and we would pixelate the face to keep it anonymous, but just outlandish profile pictures that you're like, "What is this person thinking? Why? Why are they doing this? I don't understand what's behind that." It's fascinating, again, like what led that person to doing that.
Jennifer Tracy: I'm going to back up. I was on the apps from... This is so weird. This is vulnerable. I'm talking to you guys. I don't have a guest. I'm not focusing on another person. I have to go back to what I was saying about myself, talking about this thing that I have not spoken about publicly because I wanted to be respectful of my ex-husband and my child, but there's been enough ask from listeners and friends of mine and then this thing happened that I'm like ready to, I think it needs to be talked about. I want to open up more dialogue among people about it in this way. I was on the apps from August of 2017 to December, and then I went off it. Then, I met someone. I met someone in February of 2018 at a bar. I was at my friend's gig. She was doing a show, and I met him. She knew him. He knew of me, so we kind of both knew we were going to be there at the same time, so it wasn't really a setup, but it was sort of a date, but it wasn't, but it was.
Jennifer Tracy: We fell in love. It was instant. It was magical. It was amazing. I was so surprised and shocked. Then, I got sick. I got really sick like 10 days later. I think we met for lunch a week later, and we had this really sweet lunch and walk across the street for coffee. We held hands and made plans for an evening date. Then, I got really sick, and I couldn't see him for like three weeks. All we could do was text and talk on the phone because I was just really, really sick and contagious and bleh. You know, that slow getting to know each other in that way was really romantic and really sweet and really vulnerable. Then, we dated. Then, he broke up with me in April for nothing, which I won't disclose all of that because I want to respect him as well, but he broke up with me. Then, we got back together, broke up, got back together, broke up, got back together, and finally broke up again for the last time this past March.
Jennifer Tracy: I was devastated and have been devastated but also like accepting of what is. I love this man, and I wish him well. He's a remarkable human being, and it just didn't work out. That's the way things go sometimes. It's been five months. My girl friends have been saying, "You need to get on the apps. You need to get on the apps. You need to get on the apps." My thinking has always been like, "You guys are younger than I am. You don't have kids. It just doesn't work for me." Finally, I said, "Let's get over that and try it again, Jen. Let's just be willing and see. Be vulnerable. Be willing." I did the thing, put my profile up, texting them pictures, "Is this one okay? Is this too much?" You know, I started on the thing.
Jennifer Tracy: It was literally just I did it for an hour, and I called my girl friend who was helping me do it, and I said, "I can't do this. This is just too lonely doing this. It's sad. I'm so sad. These are all people." The one I was on, I was on Tinder, just tell you I was on Tinder because they said, "Just go on Tinder. It's easy, blah, blah, blah. It's not what it used to be." When you swipe left on Tinder, which means you're saying, "No, I don't want to connect with that person," it stamps a big, it looks like it's stamping a big nope on their forehead as it swipes. I just was like, "That's so I don't know." Also, I just kind of gave into it and thought, "Well, this is part of the process. It's kind of like you're browsing for the perfect sweater. Just think of it as like a rack of clothing, and you're looking for your size and looking for the right texture. It doesn't mean the other sweaters are awful. They're just not a good fit for you."
Jennifer Tracy: That's how I kind of had to change my mentality around it. Finally, I found one or two that I swiped right with and matched with them. One or two, we didn't message. One messaged me some disgusting thing that was so inappropriate that I deleted him. Then, the other one was like appropriate and respectful and cute and funny and witty. Anyway, we ended up going out on a date, and I cried all the way home in my car last night. I had been thinking, "I need to do this episode tomorrow, today, and what am I going to talk about?" As I'm crying on the way home from this date, I'm like, "I think I know what I need to talk about," so I deleted my Tinder account this morning. Again, this man is lovely. There's nothing wrong with him. There's nothing wrong with him. He's just not my guy.
Jennifer Tracy: There's things that I wish I could give him tips on, like don't pick your food out of your teeth with your fork at the dinner table. When you bring me back to your apartment, don't walk into your kitchen and do a snot rocket into your hand in the kitchen sink and think I'm not going to know, things like that, but very handsome, very smart, very well-spoken, took me to nice places, but it just wasn't a match. I just thought I can't keep doing this. I have so many other things that I want to put my energy towards, and I calculated sort of roughly over the last 12 days I've probably spent an hour a day swiping left on this thing and then just add another total of two hours messaging these people. That's 14 hours. For me, that's about 10 podcast recordings or that's two or three articles that I could write and submit for publishing.
Jennifer Tracy: Do you know what I mean? Or it's time that I could spend sleeping or it's time that whatever. My point is it doesn't really fit into what I'm willing to have my time be based on the intention that I have set for my life, and I also want to acknowledge I know that this works really well for a lot of people. It feels good to them. It feels like a good way of life for them. It feels like a good fit, and I acknowledge that, and I respect it. I'm just listening to my body and what happens and what happened last night when I came home and just felt like hollow, and I didn't want to do it anymore so I deleted it. That's okay. That is totally okay, and more will be revealed. That is my episode on dating in my mid-40s as a single mom and kind of just little bits of what it's been like.
Jennifer Tracy: One guy, though, I wanted to added this in, I forgot to mention. I do have these somewhere tucked away. Two years ago, when I was on this, and this was on Bumble, this guy, it was so interesting. He was a musician. He was a professional musician in a symphony orchestra. He was living in LA temporarily, and he just immediately came out and said, "I'm a submissive, and I think you should be my dom, my dominatrix," because dom would be if a man is a dom, a woman is a dominatrix. I, having written a book on a woman becoming a dominatrix, having written a series of erotica under a penname, was like, "Sure. Okay." Via the messaging, we did this for like two days, but I think my assignments for him, because I've never done this professionally, were a little bit too outlandish. I mean, I kind of was messing with him because, at that point, I was already like so done for the first time with the apps.
Jennifer Tracy: Yeah, I was asking him to do, like, "Go do this and then text me back and tell me that you've done it." He kept calling me... What did he call me? He called me mam. He kept calling me mam. I was like, "Don't call me mam. Call me mistress," or whatever. Anyway, that was really fun, but yeah. Moving on, I'm going to find other ways to be vulnerable because that's the kind of partnership I want to have ultimately. There you have it. I love you guys so much, and I hope you enjoyed this episode. Join me next week for a fresh episode of MILF Podcast. Just a reminder to visit FlirtyGirlGuide.com and use the code MILF10 for your exclusive discount of 10% off any of Flirty Girl Guide's sex toys. Until then, keep going. I love you.