First Date Stories Shows Midlife Dating Can Be an Adventure

The Short Version: Through First Date Stories, single women in midlife learn that the stage of life they're in is exactly the right one. Jodi Klein writes and hosts the podcast, book, and blog that together form First Date Stories. She gathers and passes along real women's accounts of dating and romance, whether they're in their 30s, 40s, or 50s, or older, so other women in the same spot feel supported. Midlife dating comes with its hurdles, but Jodi uses First Date Stories to show it can be empowering and meaningful no matter how things turn out.

Valentine's Day has always been a favorite of mine. As a kid, I lived for the candy (obviously) and the classroom parties, and these days I use February 14th as an excuse to throw a dinner party for my friends. Plenty of people find winter long and hard, and to me Valentine's Day has always been a short break from all that, full of warm colors, even warmer feelings, and a reason to let people know you love them.

Not everyone shares that view, though. Admitting how much I love the holiday sometimes earns me a sideways look.

Usually that look comes with an “Ugh, I hate Valentine’s Day,” or sometimes “I don’t want to talk about it.” If you're single and unhappy about it, it makes sense that Valentine's Day would grate on you. Dating is tough, and tougher still once your 20s are behind you. For all its challenges, though, dating in midlife can be enormously rewarding.

Jodi Klein proves it with First Date Stories, a book, podcast, and blog she writes and hosts about the finer points of single life for women in their 30s, 40s, and 50s, and past that. Her stories and resources are for single women of every kind, whether they've never married, have just divorced, or have lost a spouse.

By showing women that plenty of others are dating in midlife too, First Date Stories helps them make sense of where they stand. Telling a story carries a special power, and so does hearing one, and First Date Stories does both. Jodi walked us through the book, podcast, and blog, then offered midlife single women some advice on handling the emotions Valentine's Day can stir up.

“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.”

We're Definitely Not in Our 20s Anymore

Jodi spent 26 years dating before she met her husband, and she said a lot of that stretch felt like going it alone. She struggled to find support and resources for women dating beyond their 20s, the very women who often need them most. Midlife dating isn't the same as dating in your 20s, and knowing how it differs helps women handle it better.

“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.”

According to Jodi, midlife daters tend to drop the “performance art” side of dating, in which singles present the version of themselves they think a prospective partner wants instead of who they actually 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.”

On First Date Stories, Jodi Klein passes along true stories from actual women.

Few things help a single person on the dating scene more than confidence, and real confidence runs deeper than appearances. The confidence Jodi means covers both how people carry themselves in public and how they see themselves inside. Older daters usually know more clearly who they are and what they want.

As for obstacles, midlife daters typically get less support from their peers than younger daters do. Jodi's book identifies what she considers the six biggest challenges, the ones she says frequently push midlife women to quit dating early or never start. “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.”

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

Obstacles like these can leave midlife daters feeling isolated and lonely, and Jodi built First Date Stories to fight that. She gives women a place to tell their stories, good parts and bad, in the hope of inspiring and supporting midlife women everywhere as they return to dating.

On the Power of Showing Up: A Book, Podcast, and Blog

Each of Jodi's three outlets gives midlife women something different, yet all of them insist that single life deserves celebrating. The book “First Date Stories: Women’s Romantic and Ridiculous Midlife Adventures” collects first date stories from real single women in midlife and pairs them with Jodi's tips and inspiration.

Not every date will end in lasting love, the book reminds readers, but each one can show a single person something worthwhile about who they are and what they want. Jodi encourages readers to go into dating with an open mind and realistic expectations. Singles who count on every date being life-changing are all but guaranteed to end up 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.”

Single women in their 40s and 50s, and older, will find First Date Stories an invaluable resource.

The focus of First Date Stories is the dating journey itself, whether it turns out upsetting, embarrassing, or flat-out 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.”

On the First Date Stories podcast, older single women get to hear from women in situations like theirs. Every episode, Jodi shares different women's romantic adventures and layers in her own 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.”

Skip the Valentine's Day Dread, and Enjoy Dating

For midlife singles unhappy with their love lives, Valentine's Day can be hard. The holiday's imagery and messaging can leave anyone who isn't in a committed relationship feeling pressured, or even inferior. Jodi acknowledged that singles may find the season difficult, but she said it isn't all doom and gloom.

In her blog post “How Not To Dread Valentine’s Day,” Jodi offers midlife women tips and ideas for getting through February 14th. The details are in her post, but a lot of her advice comes down to mindset. You might be in a spot you're not exactly thrilled with, yet if you see yourself as capable and strong, the whole thing can feel less stressful and, in time, even empowering.

Single women can live full, satisfying lives without a romantic partner, Jodi pointed out.

The same goes for midlife dating as a whole. Shifting your outlook isn't easy, though, particularly when the letdowns pile up and there's nowhere to go for guidance. That's the gap First Date Stories fills. “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.”

Women in midlife need support, plus dating resources that understand their particular circumstances and point of view. Far too often, what they hear about midlife dating, especially as women, is overwhelmingly negative. That's the message First Date Stories pushes back on, showing that older women can have dating experiences that are fun, adventurous, and transformative.

“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.”