Ask Elisa celebrates Pride Month with the first LGBTQIA+ guest! Hilary shares her story of dating women and men. I had so much fun talking with Hilary and I learned quite a bit.

As always, I share a question from a listener for my guest and me to respond to. The question for this episode is, “What do you think about having a friends with benefits relationship?”

Send in your dating dilemmas and questions to askelisapodcast@gmail.com or through social media direct messages to have Elisa and a guest share their response on a future episode.

Find Ask Elisa on social media:

• Join the Ask Elisa community on Patreon at https://www.patreon.com/cw/AskElisa
• Instagram: @askelisapodcast
• Threads: @askelisapodcast
• YouTube: @askelisa
• Tiktok: @askelisapodcast

About Ask Elisa

Ask Elisa is a podcast about dating in your late 30s, 40s, and older. I’m your host, Elisa Sparkman. I found myself unexpectedly single right before my 40th birthday. Now with two years of dating behind me, I wanna talk about it! Dating at this stage in life has its unique challenges.

Join me and my guests as we take real questions from listeners and dive into the messy, funny, and often frustrating world of modern dating—from first dates and dating apps to boundaries, heartbreak, and everything in between. Whether you’re newly single, getting back out there after years, or just trying to make sense of it all, you’ll find validation, perspective, and comfort here. Come for the laughs, stay for the honesty—and leave feeling a little less alone in your love life.

In this episode, I finally have a male guest! I talk with Kelly (who I call Boy Kelly, because one of my best friends is named Kellee and she gets to be Kellee. Hi Kellee, I love you.) Boy Kelly shares his experience as a straight man on the dating apps. I give him my permission to trash women on my show, because I know Boy Kelly would never.

As always, I share a question from a listener for my guest and me to respond to. The question for this episode is, “I’m ready to start dating again but I’m scared of rejection. And I’m scared people will be mean to me. What are some tips to work through this?”

Send in your dating dilemmas and questions to askelisapodcast@gmail.com or through social media direct messages to have Elisa and a guest share their response on a future episode.

Find Ask Elisa on social media:

• Join the Ask Elisa community on Patreon at https://www.patreon.com/cw/AskElisa
• Instagram: @askelisapodcast
• Threads: @askelisapodcast
• YouTube: @askelisa
• Tiktok: @askelisapodcast

About Ask Elisa

Ask Elisa is a podcast about dating in your late 30s, 40s, and older. I’m your host, Elisa Sparkman. I found myself unexpectedly single right before my 40th birthday. Now with two years of dating behind me, I wanna talk about it! Dating at this stage in life has its unique challenges.

Join me and my guests as we take real questions from listeners and dive into the messy, funny, and often frustrating world of modern dating—from first dates and dating apps to boundaries, heartbreak, and everything in between. Whether you’re newly single, getting back out there after years, or just trying to make sense of it all, you’ll find validation, perspective, and comfort here. Come for the laughs, stay for the honesty—and leave feeling a little less alone in your love life.

I apologize for the abrupt ending on this episode. We're new at this; mistakes happen. In this episode, I talk with Morgan. For the past three years, Morgan has chosen not to date. We talk about what it's like to be a single woman in a society that places so much value on romantic partnerships.

As always, I share a question from a listener for my guest and me to respond to. The question for this episode is, "Should people wait until a divorce is final before they start to date?"

Send in your dating dilemmas and questions to askelisapodcast@gmail.com or through social media direct messages to have Elisa and a guest share their response on a future episode.

Find Ask Elisa on social media:

• Join the Ask Elisa community on Patreon at https://www.patreon.com/cw/AskElisa
• Instagram: @askelisapodcast
• Threads: @askelisapodcast
• YouTube: @askelisa
• Tiktok: @askelisapodcast

About Ask Elisa

Ask Elisa is a podcast about dating in your late 30s, 40s, and older. I’m your host, Elisa Sparkman. I found myself unexpectedly single right before my 40th birthday. Now with two years of dating behind me, I wanna talk about it! Dating at this stage in life has its unique challenges.

Join me and my guests as we take real questions from listeners and dive into the messy, funny, and often frustrating world of modern dating—from first dates and dating apps to boundaries, heartbreak, and everything in between. Whether you’re newly single, getting back out there after years, or just trying to make sense of it all, you’ll find validation, perspective, and comfort here. Come for the laughs, stay for the honesty—and leave feeling a little less alone in your love life.

In this episode, Claudia is back to share her craziest dating story. She starts off by saying, "This story... I do think should be a Netflix show..." And I share a quick story about the audacity and self-importance of a random dude I matched with on Bumble.

Send in your dating dilemmas and questions to askelisapodcast@gmail.com or through social media direct messages to have Elisa and a guest share their response on a future episode.

Find Ask Elisa on social media:

• Join the Ask Elisa community on Patreon at https://www.patreon.com/cw/AskElisa
• Instagram: @askelisapodcast
• Threads: @askelisapodcast
• YouTube: @askelisa
• Tiktok: @askelisapodcast

About Ask Elisa

Ask Elisa is a podcast about dating in your late 30s, 40s, and older. I’m your host, Elisa Sparkman. I found myself unexpectedly single right before my 40th birthday. Now with two years of dating behind me, I wanna talk about it! Dating at this stage in life has its unique challenges.

Join me and my guests as we take real questions from listeners and dive into the messy, funny, and often frustrating world of modern dating—from first dates and dating apps to boundaries, heartbreak, and everything in between. Whether you’re newly single, getting back out there after years, or just trying to make sense of it all, you’ll find validation, perspective, and comfort here. Come for the laughs, stay for the honesty—and leave feeling a little less alone in your love life.

In this episode, I talk with Dani. Dani became a single mom in her mid-20s and over the past decade and half has stepped in and out of the dating scene. Dani shares her experience dating as a single mom, through college, grad school, working full time, and being an overall impressive human.

As always, I share a question from a listener for my guest and me to respond to. The question for this episode is, "I'm finally ready to start dating again. But my kids don't want me to. Do you have any suggestions for how to navigate this?"

Send in your dating dilemmas and questions to askelisapodcast@gmail.com or through social media direct messages to have Elisa and a guest share their response on a future episode.

Find Ask Elisa on social media:

• Join the Ask Elisa community on Patreon at https://www.patreon.com/cw/AskElisa
• Instagram: @askelisapodcast
• Threads: @askelisapodcast
• YouTube: @askelisa
• Tiktok: @askelisapodcast

About Ask Elisa

Ask Elisa is a podcast about dating in your late 30s, 40s, and older. I’m your host, Elisa Sparkman. I found myself unexpectedly single right before my 40th birthday. Now with two years of dating behind me, I wanna talk about it! Dating at this stage in life has its unique challenges.

Join me and my guests as we take real questions from listeners and dive into the messy, funny, and often frustrating world of modern dating—from first dates and dating apps to boundaries, heartbreak, and everything in between. Whether you’re newly single, getting back out there after years, or just trying to make sense of it all, you’ll find validation, perspective, and comfort here. Come for the laughs, stay for the honesty—and leave feeling a little less alone in your love life.

Bonus mini episode!

If you liked hearing me talk with Rhonda, my boyfriend's mom, in episode 5, you will love this short clip of us chatting away before we started the episode.

Send in your dating dilemmas and questions to askelisapodcast@gmail.com or through social media direct messages to have Elisa and a guest share their response on a future episode.

• Join the Ask Elisa community on Patreon at https://www.patreon.com/cw/AskElisa
• Instagram: @askelisapodcast
• YouTube: @askelisa
• TikTok: @askelisapodcast

An hour after meeting my (relatively new) boyfriend's mom, I'm sitting down and recording a podcast episode with her. Rhonda, now 66, tells the story of the worst blind date she's every been on. This episode confirms, that dating was rough before the apps. It's always been terrible, so let's just laugh about it.

Send in your dating dilemmas and questions to askelisapodcast@gmail.com or through social media direct messages to have Elisa and a guest share their response on a future episode.

Find Ask Elisa on social media:

• Join the Ask Elisa community on Patreon at https://www.patreon.com/cw/AskElisa
• Instagram: @askelisapodcast
• Threads: @askelisapodcast
• YouTube: @askelisa
• Tiktok: @askelisapodcast

About Ask Elisa

Ask Elisa is a podcast about dating in your late 30s, 40s, and older. I’m your host, Elisa Sparkman. I found myself unexpectedly single right before my 40th birthday. Now with two years of dating behind me, I wanna talk about it! Dating at this stage in life has its unique challenges.

Join me and my guests as we take real questions from listeners and dive into the messy, funny, and often frustrating world of modern dating—from first dates and dating apps to boundaries, heartbreak, and everything in between. Whether you’re newly single, getting back out there after years, or just trying to make sense of it all, you’ll find validation, perspective, and comfort here. Come for the laughs, stay for the honesty—and leave feeling a little less alone in your love life.

Do you have a dating story you’d like to have featured on a Dating Storytime episode of Ask Elisa? Send in a written version of your favorite dating story for me to read on the show to askelisapodcast@gmail.com.

I also take questions from listeners. This can be a simple question about dating etiquette or sharing a dating dilemma you’re facing you’d like some feedback on. Send in your questions to askelisapodcast@gmail.com.

New episodes every Thursday.