First Date Stories Explores Midlife Dating

Women's Dating

First Date Stories Proves That Midlife Dating Can Be Full Of Adventure & Meaning

Chloë Hylkema

Written by: Chloë Hylkema

Chloë Hylkema

Chloë Hylkema loves using her writing skills to tell stories that matter. Her time as an English student at Emory University molded her into a detailed writer with a knack for the relatable. Chloë is familiar with what it means to date in the modern age, and she endeavors to write material that is both truthful and helpful. She has previously worked as lead campaign writer for an animal advocacy group and now brings her passion for engaging and actionable content to

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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The Short Version: First Date Stories shows single midlife women that where they are in their lives is just right. Jodi Klein is the author and host of the book, podcast, and blog that make up First Date Stories. Jodi collects and shares the stories of real women navigating dating and romance in their 30s, 40s, 50s, and beyond to support other women like them. While dating in midlife can have its challenges, Jodi is using First Date Stories to prove that the experience can be empowering and meaningful, regardless of its outcomes. 

I’ve always loved Valentine’s Day. The candy (obviously) and classroom festivities were my favorite part of the holiday as a child, and now I take February 14th as an opportunity to have a dinner party with my friends. Winter can be a long and difficult season for many people, and I’ve always seen Valentine’s Day as a brief day of respite that’s filled with warm colors, warmer feelings, and an excuse to tell people you love them.

But this isn’t necessarily a popular opinion. Sometimes, I get a sideways glance when I express my love for the holiday.

It’s usually followed by, “Ugh, I hate Valentine’s Day,” or even “I don’t want to talk about it.” If you’re single and not thrilled about it, it’s understandable why Valentine’s Day would be an annoying event. Dating can be hard, especially when you’re not in your 20s anymore. Even with all of its challenges, dating in midlife can be a deeply rewarding experience.

First Date Stories is Jodi Klein’s way of proving it. First Date Stories is a book, podcast, and blog authored and hosted by Jodi that explores the nuances of being a single woman in her 30s, 40s, 50s, and beyond. Jodi has stories and resources for single women, whether they’ve never been married, are recently divorced, or are widowed. 

First Date Stories helps women understand their own dating situation by showing them they aren’t alone in midlife dating. There’s a special power in telling a story, and there’s also a special power in receiving a story, and First Date Stories is doing both. Jodi talked to us about her book, podcast, and blog and gave single women in midlife some advice for navigating the feelings that may arise around Valentine’s Day. 

Don’t let Valentine’s Day get you down,” Jodi said. “It can be a challenging holiday for a lot of people, but there are plenty of ways to make it better.”

I Have A Feeling We’re Not In Our 20s Anymore

Jodi dated for 26 years before finding her husband, and she said much of this journey felt like a solo adventure. She had a hard time finding resources and support for women dating out of their 20s and who often need these things the most. Dating in midlife is different from dating in your 20s, and the more women know about the differences, the better they can navigate them.

“There are tremendous things about dating in midlife,” Jodi said, “and there’s also some challenges. One of the amazing things is that you know yourself so much better than you did when you were in your 20s or 30s, so you’re more likely to show up as yourself.”

Jodi said midlife daters often leave behind the “performance art” aspect of dating, where singles show up in a way that they think a potential partner will like rather than as they really are. “You’re more confident, but you’re also more interesting because you’ve had more life experiences,” she said. “You have more to say, and you have this potential to make connections on a different level than you were when you were younger.”

first date stories founder jodi klein
Jodi Klein shares real stories from real women on First Date Stories.

Confidence is one of the greatest assets a single person can have while dating. And confidence goes further than skin-deep. The kind of confidence Jodi referred to has to do with how people present themselves outwardly and how they view themselves internally. Older daters often have a clearer sense of who they are and what they’re looking for.

In terms of challenges, midlife daters often don’t receive the same peer support as younger daters. In her book, Jodi identifies the six biggest challenges which she says often cause midlife women to drop out of dating early or never pursue it at all. “You just don’t have the same level of support as you did in your 20s and 30s. You don’t have wingwomen and wingmen around, because they’re often at a different stage of life.”

Jodi said another obstacle was finding time to date. “One of the biggest challenges is time,” she said. “Because your life is so much busier and complicated than it used to be.” 

These challenges can make midlife dating an isolating and lonely experience. Jodi created First Date Stories to combat that. By giving women the platform to share their stories – the highs and the lows included – Jodi hopes to give midlife women everywhere the inspiration and support they need to get back into dating.

A Book, Podcast, And Blog About The Power Of Showing Up

Jodi’s book, podcast, and blog each offer something different to midlife women, but each is insistent that being single should be celebrated. “First Date Stories: Women’s Romantic and Ridiculous Midlife Adventures” is an anthology of first date stories from real midlife single women, along with tips and inspiration from Jodi. 

The book shows readers that while every date may not lead to everlasting love, each date can teach a single person something valuable about themselves and what they’re looking for. Jodi urges her readers to approach dating with openness and appropriate expectations. If singles expect every date to lead to something life-changing, they will almost certainly be disappointed. 

“It’s so important to just keep showing up for first dates,” Jodi said. “It’s about putting yourself out there in the world. The truth is, nobody needs a partner to have a very rich and fulfilling life. But if that’s important to someone, I want to tell them to keep going and enjoy the journey.”

first date stories podcast and blog
First Date Stories is an invaluable resource for single women in their 40s, 50s, and beyond.

First Date Stories is about the journey of dating, even if that journey is upsetting, embarrassing, or downright hilarious. “There’s going to be disappointments, there’s going to be challenges, and there’s going to be a lot of laughs and great stories,” Jodi said. “If you can just get one thing out of each first date, learn something new, get a good joke– anything– then it’s worth the experience because it reaches you.”

The First Date Stories podcast gives older single women the opportunity to hear the stories of women similar to them. Jodi presents the stories of different women and their romantic adventures for each episode and adds her insights and takeaways. 

“I think women have a superpower of helping each other and supporting each other,” Jodi said. “It’s one of our powers, and I think we all need to use it. Because when we lift each other up, that’s the greatest gift we can give to each other. Having spoken to so many women and heard their stories, I know it makes other women feel like they’re part of the midlife posse, and, most importantly, they’re not alone.”

How Not To Dread Valentine’s Day – And Enjoy Dating

Valentine’s Day can be troubling for midlife singles who aren’t happy with their romantic situation. The imagery and messaging around the day can make people who aren’t in committed relationships feel pressured or even inferior. Jodi said while this can be a challenging time for singles, it’s not all doom and gloom.

Jodi’s blog post, “How Not To Dread Valentine’s Day,” gives midlife women advice and ideas for navigating February 14th. You can find the specifics in Jodi’s piece, but much of the advice she gives has to do with mindset. You can be in a situation that you’re not necessarily thrilled about, but if you have an outlook that recognizes your ability and strength, the situation can become less stressful and eventually empowering.

jodi klein advice for valentines day
Jodi reminded single women they can have complete and fulfilling lives without a romantic relationship.

This is true for the entire experience of dating in midlife. But it can be hard to change your outlook, especially when disappointments keep coming and you don’t have a place to turn for guidance. This is where First Date Stories comes in. “So many women feel alone in this stage as they’re looking for a partner,” Jodi said. “They need support that’s unfortunately not available to them. First Date Stories is trying to fill that void.”

Midlife women need support and dating resources that understand their unique situation and perspective. All too often, the messaging around dating in midlife, especially for women, is overwhelmingly negative. First Date Stories is pushing back against that and proving that older women can have transformative, adventurous, and fun dating experiences.

“I always tell women to get out there,” Jodi said. “Actually going to events, going out in the world, traveling, joining groups of other women, getting involved in the community, are the best things they can do for themselves. It’s not all about dating and romance, it’s about living a fulfilling life.”