Dating is a wild ride. If you’ve ever found yourself on a date with someone who speaks about themselves in the third person—yeah, I’ve been there—then you know the struggle is real. In the latest episode of the Pure Intentions Podcast, Sir Anthony and I dive deep into the hilarious, awkward, and sometimes downright bizarre dating experiences we’ve all endured. From competitive dates at Puttshack to romantic surprises, our stories reveal a lot about navigating relationships and staying true to yourself.
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The Worst Dating Experiences (and What We Learned)
When it comes to bad dates, I’ve had my fair share. I’ll never forget the guy who took me for jerked chicken and referred to himself in the third person all night. At first, I laughed it off, thinking it was a joke. But when he kept it going? Yeah, I knew there wouldn’t be a second date. As I shared in the episode:
“I don’t know if he did it because I laughed at it the first time, but it was weird as hell. It was definitely giving no second date.”
But here’s the thing—these experiences teach us something valuable. Relationship therapist Dr. Laura Berman once said, “Bad dates are simply detours on the way to finding what truly resonates with you.” Every awkward or disappointing encounter serves as a mirror, helping us understand our values, deal-breakers, and communication styles.
The Role of Societal Pressures in Dating
Dating in today’s world comes with a whole lot of societal baggage. There’s this pressure to conform to expectations around age, body count, and even the so-called “perfect” relationship. We talked about how questions around age often feel invasive, yet necessary. As I said in the episode:
“Aging is a beautiful thing… to know that you’ve successfully lived a full life, why wouldn’t you want to disclose your age?”
I’ve always been curious why women are reluctant to share their age. As Sir Anthony puts it, “You never ask a woman her age… let her offer it to you.” With that stated… Ladies, please inbox us anonymously and tell us why you don’t want to disclose your age.
But the reality is, societal norms can make people feel insecure about things that shouldn’t even matter in a meaningful connection. According to relationship expert Esther Perel, “We carry cultural scripts about love and relationships that often don’t serve us in real life.” The takeaway? We need to define love on our own terms and not let outside noise dictate our journey.
Social Media and Dating Culture: A Blessing or a Curse?
We can’t talk about modern dating without acknowledging the influence of social media. From Instagram to reality TV, these platforms create unrealistic expectations, making it harder to appreciate genuine connections. Sir Anthony shared his thoughts on this during the episode:
“Social media doesn’t show you the work that goes into a relationship; it just shows the goals and the happy moments.”
While it’s great to celebrate love online, it’s important to remember that relationships are built offline—with real conversations, shared experiences, and mutual growth.
Swipe Right or Left on Love?
Dating apps have completely transformed how we connect with potential partners. They offer instant access to a wide pool of people, but they also come with their own set of challenges. I’ve had my fair share of experiences with online dating—some good, some weird, and some that made me question my entire life choices. As I shared in the podcast:
“I do believe that you can find something on a dating app. I know a couple of couples that got married and had babies meeting somebody off a dating app.”
Platforms like Hinge and Bumble can be great for meeting people, but they also require intentionality. It’s easy to get lost in endless swiping and superficial conversations, but finding a meaningful connection means knowing what you’re looking for and setting boundaries from the start. And let’s not forget—being mindful of red flags is key. Some people are only there for a good time, not a long time.
While I personally recommend Hinge for its more thoughtful approach to matchmaking, I’ve learned that success with online dating often depends on the energy you bring to it. Whether you’re looking for something casual or long-term, asking intentional questions can help weed out those who aren’t on the same page. As Sir Anthony mentioned in the episode:
“We actually have a list of great Hinge prompts on our website, so you can ask the right questions and get straight to what really matters.”
Of course, with dating apps comes the challenge of authenticity. It’s easy to fall for someone’s carefully curated profile, only to realize they’re completely different in real life. The key is to remain authentic and approach online dating with a sense of curiosity rather than pressure.
If you’re dating online, remember to have fun, stay safe, and always trust your gut. And if you need a little help navigating the conversations, check out our Beyond Dating Deck, designed to help couples build meaningful connections beyond the surface level.
The Importance of Self-Discovery in Relationships
One of the biggest lessons I’ve learned? You have to know yourself before you can truly connect with someone else. So many people enter relationships without fully understanding their own needs and boundaries. And trust me, I’ve been there.
“I didn’t start enjoying relationships until I learned to love myself first.”
This is where tools like our Sister Circle Friendship Deck come in handy. They encourage honest, meaningful conversations that help you connect with yourself and your friends on a deeper level.
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