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Entrepreneur’s lonely heart led to new business venture

Off The App Dating helps Fox Valley singles find real connections through events, personalized matchmaking

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January 12, 2026

NORTHEAST WISCONSIN – Cassandra Lambert, founder of the new Off The App Dating service, said she spent years navigating online dating apps in her personal quest for love – admitting the journey wasn’t always easy.

Although she eventually found love and is now enjoying her roles as wife and stepmom, Lambert said her earlier online dating experiences revealed a gap in the Fox Valley for singles – one she was determined to fill.

“We were actually at our first anniversary dinner [when the idea came to me],” she said. “Honestly, I stopped mid-sentence – my husband was sitting across from me at the table – and I said, ‘I have it. I have the idea.’”

Lambert said she credits her husband – whom she calls a “brilliant” businessperson – for helping get Off The App Dating off the ground.

“He knew exactly how to help me with my LLC and how to get my EIN,” she said. “He was like, ‘We’re going to do this, this, this and this.’ I’m not built like that. I am the idea woman, and he is the business numbers man. He got me my business bank account, and I was set – in a matter of days. I thought, ‘We’re doing this, and I’m not looking back.’”

Early years that shaped a matchmaker

After attending Fox Valley Lutheran High School in Appleton, Lambert – a Greenville native – said she went on to study sales, marketing and event planning at Fox Valley Technical College (FVTC) before earning a bachelor’s degree in hospitality and tourism management from the University of Wisconsin-Stout.

Growing up in a family rooted in hospitality – her father has taught culinary arts at FVTC for more than 30 years – Lambert said, helped shape her own passion for the industry.

“I grew up in a hospitality-focused household,” she said. “My parents always hosted dinner parties and had friends over. And my dad loves to cook and share his passion for food. It was just normal for us to have parties and gatherings. And I knew I loved being around people.”

A self-described social butterfly, Lambert said she thrived on the social scene in high school, often prioritizing friendships over academics.

After graduation, she said her first job as a bartender gave her the opportunity to get to know people while discovering her passion for serving and supporting others.

“When others around me are doing well, I feel a sense of accomplishment,” she said.

Lambert said her desire to create a sense of comfort and care for others naturally led her into the field of hospitality.

Over the past 15 years, she said she has honed her passion through various hospitality management roles – except for a few years at Thrivent Financial during the COVID-19 pandemic, when she lost her full-time management position.

However, Lambert said she quickly realized the remote work didn’t provide the social interaction she thrives on. 

“It was such a shell shock to me,” she said. “I knew I needed more.”

So, to satisfy her need for social interaction, Lambert said she returned to hospitality as a server, working three nights a week while keeping her full-time job.

Though she ultimately returned to hospitality management full-time, Lambert said the move was short-lived.

She said she soon had an “aha” moment, recognizing that the business model behind Off The App Dating was an idea she had been sharing with friends for more than a decade.

“It was like God led me there,” she said.

Describing herself as an “active dater” – not marrying until her 30s – Lambert said she was online dating for more than 16 years.

“I went on dates on the nights I had off,” she said. “It was very important to me to find a God-fearing spouse. And boy, was I looking. It was a lot.”

As she recounted her dating stories to her girlfriends, Lambert said she often joked that some of the men she met online “needed help” when it came to the art of dating.

“Their photos were outdated and the grammar on their profiles [was incorrect],” she said. “Maybe it was just a lack of confidence. I have said this for years: I would love to be a consultant and take them to some fun locations and take real, authentic photos and not posed mirror selfies – to [help] boost their confidence.”

Cassandra Lambert said before launching Off The Date App and online dating herself, she would look for singles events, but the nearest ones were in Chicago or Minneapolis. Submitted Photo

Along with online searches, Lambert said she looked for dating events, but the closest were always in Chicago or Minneapolis, making them impractical for a young professional in the Fox Valley with a demanding schedule.

“I didn’t want to travel oodles of hours to go find someone,” she said. 

Drawing on her passion for hosting and event planning – responsibilities she had already embraced during her time as a bar manager – Lambert said she began reflecting on her dating experiences and how she could potentially create warm, welcoming and safe spaces for single people to connect offline. 

“I’m so anti-tech,” she said. “I know it’s the direction [things are going]. But it’s so important not lose that human element and to remind people to go beyond the ‘norm’ of finding someone online. So, it all morphed into wanting to host singles’ events. And then it really quickly became, ‘Oh, I should look into becoming a matchmaker.’”

Now a certified professional matchmaker, Lambert said she offers both matchmaking services and singles events across the Fox Valley.

Singles events

For many singles in the area, Lambert said, the alternative is often just staying home. 

Off The App Dating events, she said, give people a safe and enjoyable way to meet and interact with other locals in their own communities – and early results suggest the events are resonating. 

“Whether it’s been someone looking for a date or looking to date with intention, Off The App Dating events takeaways have been wonderful,” she said. “We are doing a lot of growing, but the response to those who have trusted me enough to put their hard-earned money toward an event ticket has shown up and thanked me for the event. They are very sincere…. That’s my ‘why’ – everyone deserves love.”

Going through the journey herself, Lambert said she understands the challenges many singles face: the frustration, the hopelessness and the desire to find a partner for family life.

For many, she said, online platforms simply weren’t working.

Lambert said for her, online dating felt like a second full-time job – coming home after work only to spend hours navigating repetitive small talk and trying to maintain conversations that didn’t seem to lead anywhere.

She said she also faced unwanted challenges, from unsolicited photos to inappropriate messages, making the whole experience frustrating and exhausting. 

“I invested a lot of my time into the online dating world because it was important for me to find someone,” she said. “And I didn’t want to settle.” 

With strong family values at the core of her upbringing, Lambert said she was careful to ensure any partner she chose would fit harmoniously within her family structure.

Even with the challenges she faced, Lambert said online dating led to some memorable dates and meaningful connections – with each experience serving as a building block toward her right match.

Matchmaking

Lambert said she makes it clear to clients that matchmaking is an investment of both money and time.

As part of the process, she said she learns each person well – their personality, preferences and values – to build a complete picture of the kind of partner they’re looking for.

Lambert said she encourages her matchmaking clients to focus on what they want, rather than what they don’t want. 

“What would you love to come from this?” she said. “Are you looking more for companionship? Or are you looking to date with intentions in hopes of finding a spouse and potentially a partner to raise children with? The more that I understand, the better I can understand who I am looking for.” 

After gaining a deep understanding of her clients, Lambert said she starts actively seeking matches for them – searching within her own database and, when needed, working with other matchmakers to increase the chances of finding the ideal partner.

An investment in love

Lambert said her matchmaking services are priced at a fraction of what clients would pay in larger cities, with singles events generally ranging from $40 to $50, depending on the location and what’s included.

Admission, she said, typically covers entry, one drink, light refreshments, games and speed-dating activities.

Charging a fee, Lambert said, tends to weed out participants who may not necessarily take dating seriously.

Since launching Off The App Dating last year, Lambert said she has hosted several events, including a holiday-themed ugly Christmas sweater gathering and a cooking event focused on making fettuccine alfredo, which she dubbed “A Taste of Matchmaking.”

Cassandra Lambert said she also matches prospective partners based on what they want, as compared to what they don’t want. Submitted Photo

Personal matchmaking packages, she said, range from $3,500 to $15,000, and are based on tier.

Lambert said all packages provide one-on-one coaching, a set number of guaranteed introductions and follow-up support.

Some premium tiers, she said, also include online profile makeovers, styling services, professional photo shoots and unlimited VIP access to Off The App Dating events.

Lambert said one introduction alone can take 15-20 hours of work, from searching databases to contacting other matchmakers, who charge a standard $250 per referral.

“I think the COVID-19 pandemic kind of forced us into becoming so comfortable being home, putting our jammies on and never leaving the couch,” she said.

In a world shaped by convenience and technology, Lambert said singles can’t wait for opportunities to come to them.

Success in dating, she said, requires actively putting yourself out there.

“You have to expect that someone’s not going to come knocking on your door and say, ‘Hey, are you single?’” she said. “You have to put yourself out there in some way… Speed-dating has been around since the 1990s, and matchmakers have been around for centuries. It’s not a new concept. It’s just new to our area.” 

Lambert said her goal with Off The App Dating is to provide a different outlet – one that restores human connection in a world increasingly dominated by technology.

“I was very lonely for a long time,” she said. “A lonely heart is just something you can’t put words to unless you know what it’s like. I’ve been at family functions when Grandma and Grandpa reminded me that it’s another holiday, and I was still single. That doesn’t feel good. And it wasn’t for a lack of trying.”

Lambert said those moments motivated her to help others build meaningful connections.

More information can be found at offtheappdating.com.

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