What Went Right Series- Jenny & Tony's Online Dating Meet Cute

Welcome to Connectedness, everyone. This is a very special episode. As you may know, Connectedness is a podcast about being human together, where we talk about relationships, dating, personal growth, and generally connecting with each other.

I'm your host, Fernanda, founder of Filled Cups, and today I have two very special guests with me: my friends Tony and Jenny. I've always wanted to have them on to talk about their relationship and how they met. Last week, after being in a singles discussion, I was inspired to start a series highlighting what went right for people who found success with online dating.

Tony and Jenny are my first guests for this series. I’ll hand it over to you both: Can you introduce yourselves, share how we know each other, and tell us when you met?

I was the gateway for this friendship group. I met Fernanda before I met Tony, I believe back around 2010. I was newly single and went to a French language meetup where I met Fernanda. We hit it off, and I promptly left the meetup scene to join her fun group parties. It was a really special, blossoming time in my life. Tony and I met in 2013 and have been serious ever since.

I’m Tony, originally from California. I've lived in Illinois for more than half my life, which is what brought me to Jenny. I had been dating on and off using apps with little success—nice dates, but not really connecting.

Then I found her through a dating app, even though our paths would not have crossed otherwise. I'm forever thankful for that. When we first connected, we chatted a lot via phone and messaging, and we finally met in person about a month after we started talking.

Your Halloween party was my coming-out party to you and your friend group.

That's right! We went as "French Kiss," based on the meme at the time where you wore Kiss band makeup, carried French bread loaves, and wore berets.

It was a fantastic party, and meeting all of your friends was great. Even though nobody knew what my real face looked like under the makeup, it went really well.

The hilarious thing is how memory gets distorted over time. In my memory, Tony, you were dressed as a traditional mime with the striped shirt and the little beret!

Indeed, I think he bought a kit from Halloween City. It was a great time, and that was very early in our relationship.

It was a magical time with those house parties. Tony, when you joined that party, how early was that into your dating?

It was about a month and a half in.

That's very fresh! Jenny, you were so courageous to bring him to a party that early. Luckily we all loved Tony, but that can sometimes be a risky test.

It really was a proof-of-concept test: How does he do socially with my friends?

And you passed, Tony!

Thirteen years later! We met in the fall of 2013. Our anniversary is September 14th, right before that Halloween party.

Both of you were divorced, and Jenny, you were co-parenting your children from your previous marriage. Tony, you had a great relationship with your ex-wife, and both of you had been on dating apps. Tony, had you been on the apps longer?

Likely, on and off. After dating someone semi-significantly, I would usually cool off, separate myself from the app, and re-engage later.

Taking breaks from dating apps is so common. People get tired of the dynamic, or the pool of people starts feeling recycled, so they step away for a few months. Tony, were you always on the same app?

Initially I was on Match.com, and then I switched to OkCupid. Jenny was the first person from the apps that I dated significantly beyond just a couple of dates.

Jenny, what was your experience with the apps?

I tried Match and OkCupid. I thought Match was superficial—it felt like, "You're going to love Bob because you both like tennis."

At the time, OkCupid was a great fit for both of us because we are wordier people, and so much of dating is about self-discovery. OkCupid had extensive questions you could answer. It felt much more interesting than the modern swipe-based apps.

I was dating semi-covertly because I had an eight-year-old and an eleven-year-old. Being a child of divorce myself, I remembered what it was like switching houses and integrating new partners into family life. As Tony and I got serious, I was very protective of that boundary with my kids.

That makes total sense. When I dated Frank, I waited a long time before introducing him to my kids because I didn't want them getting attached prematurely if things didn't work out. It’s a delicate process when kids are young.

Letting the relationship bloom on its own before adding the extra pressure of parenting dynamics really worked for us. While it was okay to introduce Tony to friends early on, holding off with the kids protected them.

Early on, when my mom and kids were around, Tony was listed in my phone under a code name so the kids wouldn't pry. We hadn't formally introduced him to the family until about ten months into dating, well into the spring.

A common complaint from single people dating a parent is that they feel deprioritized or struggle with having limited access to their partner. Having been the parent, my advice is always to use that off-time to enjoy your own life and independence. How did that dynamic feel from your perspective as the partner without kids, Tony?

Since they shared custody on a two-week rotation, I knew our schedule: two weeks with kids, two weeks without. During the family weeks, we stayed in touch over the phone, text, and Skype, and then we would see each other during the alternate weeks.

For me, it acted as a gradual merge lane. I was used to being on my own 100% of the time, so this allowed me to ease into the relationship slowly.

"Merge lane" is such a great phrase for that.

When you date someone with children, you have to realize that you are eventually joining a family system, not just dating an individual in a vacuum. You are borrowing the private time of a parent, and if you become serious, you will be in a group dynamic that requires mature decisions.

If that isn't something you can embrace with love, it’s best to be honest with yourself and not date parents.

Knowing yourself and being honest upfront saves everyone a lot of heartache.

Tony has been an incredible, steady partner and a backbone for our family, especially working from home and being mindful of what we all needed.

Taking you back to OkCupid: Who reached out first, and what did that initial interaction look like?

Whenever I went back on the app, Jenny was always at the top of my list as a 98% match. I kept wondering why I hadn't messaged her, and then I would read her profile and see that I was outside her preferred age range.

I had committed to never messaging someone if I didn't meet their stated criteria because I didn't want to violate their boundaries. So every time, I'd think, "What a shame," and move on.

Were you too young for her range?

No, I was slightly older than the range she had set!

My first husband was ten years older than me, so I had set a tighter age preference just to test a different variable. Eventually, I came across Tony's profile myself.

His profile gave me warm fuzzies—nothing off-putting at all. I reached out to him during a busy, stressful period in my life, so my initial message was brief. He was very responsive and conversational.

Shortly after, I felt overwhelmed with life logistics and told him I was taking a break from the app, but I gave him my email address so we could stay in touch.

My very first email to her was: "I'm not in your age range!" I wanted to make sure she realized that, since I had been respecting that boundary for so long. Once she confirmed it was fine, we were off to the races.

What won me over early on was that he actually wanted to talk on the phone. Before our first in-person date, I remember sitting in my car in a Trader Joe's parking lot while my mom watched the kids at home, having this wonderful, long conversation with him.

My advice to daters: drop the reliance on endless texting and actually talk to each other so you can hear each other's voices.

The voice matters so much. Plus, Tony is a skilled speaker, so I'm sure his conversational style was very charming.

We also set up a video call on Skype back then. I hid in my bedroom closet late at night after the kids were asleep so we could talk.

Beyond being well-spoken, what truly won me over was his humor. He did this hilarious bit pretending to walk in zero gravity right on camera. He was uniquely goofy, and he made me laugh.

We're both silly, and we share a lot of laughter together.

Only a handful of couples I know have met online and stayed happily together long-term. With all the negativity around dating apps today, what do you think you two did differently when evaluating each other?

I went on enough dates to become clear about what worked for me and what didn't. I listened to what the people I dated wanted, and I paid attention to the horror stories they shared about other experiences so I could avoid those missteps.

When I read Jenny's profile, she checked every box and more. Online dating can easily become a fantasy realm because profiles are brief and people project their desires onto them. Having honest self-assessment makes all the difference.

Some people advise keeping dating profiles vague so you don't screen people out, but I was hyper-specific. I shared a lot of my actual personality, values, and humor.

That might have filtered out people who were intimidated or incompatible, but it attracted the right match. Tony and I were aligned on our core values and life views, which gave us a green light from the start.

Being detailed and authentic in your profile isn't about being picky; it acts as a healthy filter for values and compatibility.

I was very straightforward about what mattered to me, including being politically liberal and an atheist. We didn't need to share the exact same childhood background to share the same underlying values.

Tony brought a tremendous well of compassion, and it felt safe and healing to be accepted as I was. In a lasting partnership, emotional security and genuine friendship are just as vital as physical attraction.

I once read advice from a woman who said, "Pick the person you want to stay up all night talking to." Don't settle for less than someone you genuinely like as a human being.

When you first started dating, would you say you were both securely attached, or was that something you had to navigate?

I don't think I've ever felt anxiously attached with her. In other relationships I might have felt insecure, but with Jenny, that anxiety was never an issue.

I lean securely attached, though I've managed general anxiety. One thing I've always avoided is giving the cold shoulder. If we disagreed, I would communicate: "This is what I'm feeling, and this is what I need right now." Leaving your partner in the dark creates unnecessary anxiety, so owning your emotional state is essential.

What is your closing piece of advice for people searching for their person?

Be clear on who you are and what you want. Don't try to force compatibility.

Each dating experience can teach you what you truly need. You can negotiate the small preferences, but getting clear on the foundational values is what leads you to the right partner.

Be willing to examine your relationship patterns. Some people confuse constant drama or jealousy with passionate love.

Do the internal work so you don't automatically rule out good people. Be open to a second date before making a definitive judgment, because first-date nerves can mask who someone really is.

When you do realize someone isn't a fit, be honest and direct rather than ghosting. A peaceful, respectful parting is better for everyone.

Lastly, practice mindfulness while dating. When you find yourself overthinking or jumping ahead, take a deep breath and stay present with the person in front of you.

Mindfulness really does sit at the center of everything.

Thank you both so much for sharing your story and your wisdom on online dating. To everyone listening, thank you for tuning in to Connectedness. Feel free to reach out on social media or in the comments with your thoughts, stay safe, and stay connected!