Meet the Lessans Family

September 30, 2026 | People in Our Neighborhood

For Jenna and Greg Lessans, PJ Library Baltimore isn’t just where they live. It’s home in every sense of the word.

The two grew up in Pikesville and met while attending Pikesville High School. After Greg graduated from medical school in Baltimore, his training took the couple to several different cities. Seven years later, in 2023, they found their way back home.

Today, Jenna and Greg are raising their three children, Alana, 9 (almost 10!), Max, 7, and Zachary, 4, surrounded by the family and Jewish community that shaped their own childhoods. Greg’s parents even live right across the street.

And as they settle back into Baltimore life, they’re creating a Jewish home that blends the traditions they grew up with and the new memories they’re making together.

From Grandma’s Shabbat Table to Their Own

Some of Jenna’s earliest and most meaningful Jewish memories were made around her grandmother’s Shabbat table.

Growing up in a Conservative Jewish home, Jenna attended Rosenbloom Religious School three days a week. But some of her most lasting Jewish education happened every Friday night.

Her paternal grandmother was the matriarch of the family, an active member of Chizuk Amuno, and an incredible cook and host. Each week, about 10 family members gathered around her table for homemade challah, matzah ball soup, turkey with sliced cranberries, and homemade applesauce.

Attendance wasn’t exactly optional. Her grandmother believed deeply in bringing everyone together.

Years later, Jenna remembers much more than what was on the menu. She remembers what it felt like to know that Friday night meant family.

Today, Jenna and Greg are carrying that feeling into their own home. Friday nights are often spent around a Shabbat table, either at home or with Greg’s parents. For Jenna, raising Jewish children means helping them understand where they come from, take pride in their Jewish identity, and develop a genuine connection to Jewish traditions and customs.

Connecting Their Children to Israel

The Lessans children’s Jewish identities are also deeply connected to Israel.

Greg’s father was born in Baltimore and made aliyah when he was younger. After serving in the Israel Defense Forces, he returned to the United States and met Greg’s mother, who converted to Judaism before Greg was born.

Today, the family maintains deep roots in Israel, where Greg has an uncle, five first cousins, and approximately 30 second cousins.

Those relationships played an important role in Jenna and Greg’s decision to send their children to Krieger Schechter Day School. They wanted Alana, Max, and Zachary to receive a strong Jewish education, learn Hebrew, and be able to build meaningful relationships with their Israeli relatives.

Two Sukkahs, One Special Tradition

One of Jenna’s favorite family traditions happens every fall, when not one, but two sukkahs go up in front of the Lessans home.

The sukkahs were a gift from Jenna’s stepfather, who shared that some of his happiest Sukkot memories came from opening his sukkah to friends. He wanted Jenna and her family to experience that same joy.

Now, the Lessans family continues the tradition, filling their sukkahs with family, friends, and plenty of opportunities to celebrate together.

It’s one of the reasons Sukkot has become Jenna’s favorite Jewish holiday. There’s something special about opening their home, or in this case, their sukkahs, to the people they love and giving their children the chance to grow up with those memories of their own.

Jewish Stories Before Bed

Books are another way the Lessans family brings Jewish traditions into everyday life.

PJ Library books are part of Alana, Max, and Zachary’s regular bedtime rotation, giving the family a chance to wind down together while bringing Jewish stories, holidays, and values into their nighttime routine.

Family favorites include The Shabbat Box, Engineer Ari and the Rosh Hashanah Ride, The Old Woman Who Swallowed a Dreidel, and The Little, Little House.

Helping Other Families Find Connection

Jenna’s commitment to Jewish connection extends beyond her own family.

As a parent at Krieger Schechter Day School, Jenna was invited by the school’s Admissions Office to become a Partner Connector with The Jewish Connection Network. In that role, she helped other families discover opportunities to connect with one another and with Jewish life in Baltimore.

That experience eventually led to another new chapter. Jenna joined The Network staff as a part-time Program Assistant, where she now helps with the details and logistics that bring programs and community experiences to life.

Beyond Jewish Life

Of course, Jewish life is only one part of what keeps the Lessans family busy.

They’re devoted Baltimore Ravens fans and season ticket holders, avid bikers, and passionate travelers. Alana is even part of a bike team!

The family loves spending time at the beach and taking trips to Florida during school breaks. Closer to home, Irvine Nature Center and The Shops at Kenilworth are two favorite destinations.

When they’re staying in, family movie nights often mean Toy Story, while Bluey is a TV favorite. When they head out for dinner, Mexican food is usually at the top of the list, especially Mucho Gusto.

Jenna is also an avid reader, with The Kite Runner among her favorite books. And amid the busyness of work and family life, she’s found something she loves doing just for herself: tennis. She picked up the sport about two years ago and now plays at Coppermine as often as she can.

Coming Home

For Jenna and Greg, returning to Baltimore has meant more than coming back to the place where their own story began. It has given them the opportunity to surround their children with family, connect them to generations of Jewish tradition, and create the kinds of memories they hope Alana, Max, and Zachary will carry into their own lives someday.

The setting may have changed from Jenna’s grandmother’s Shabbat table to the Lessans family’s home across town, but the heart of it remains much the same: family, tradition, connection, and the joy of being together.

We’re so happy to celebrate the Lessans family as this month’s PJ Library Mishpacha of the Month!