Millsaps Matchmaker: Alumni Spotlight on Lily Womble

Joey Lee

August 31, 2024

"Millsaps is a rich ground for figuring out what you want from your life."

Lily Womble’s journey from a European Studies major at Millsaps to becoming a successful entrepreneur and feminist dating coach is a testament to the power of the education, support and collaborative atmosphere at the college.

A 2014 graduate, Lily reflects on her time at Millsaps, emphasizing how the institution’s unique environment and emphasis on critical thinking provided her with the tools and confidence to pursue her dreams.

She chose Millsaps not just for the academic offerings but for the sense of community and the college’s impact-driven curriculum. “Millsaps was trying to make the city of Jackson, and the world, a better place,” she recalls. This focus on making a difference in the world resonated with her.

Lily majored in European Studies with a minor in French, a path she largely designed herself with the help of supportive faculty members like Dr. Amy Forbes. “I sort of created my own path because I wanted to do international relations, and that was the closest thing,” she explained.

The flexibility to shape her educational journey was pivotal. With the guidance of professors, she developed a curriculum that not only aligned with her interests but also set the foundation for her future success.

The encouragement of her creativity and independent thinking she received while at Millsaps proved invaluable as Lily moved forward in her career. After graduating a semester early, she got a job at a nonprofit in San Francisco, a position she landed thanks to the intentional connections she made during her time in school

Lily’s drive to immerse herself in learning and surround herself with people she admired was evident as a student. “I was single-mindedly focused on learning and putting myself in rooms with people that I admired,” she said, recounting how she traveled to New York City for a Women in the World conference during spring break, which led to networking opportunities that helped launch her career.

However, her journey was far from linear. After a. year in San Francisco, she pursued her lifelong dream of living in New York City and pursuing musical theater. The path wasn’t easy – auditioning while juggling multiple side jobs, including working as a nanny and even making balloon hats at a Times Square restaurant.

It was in NYC that Lily found her true calling in a somewhat unexpected field, matchmaking.

She initially dismissed the idea of matchmaking, thinking it was frivolous, but Lily soon found that helping women navigate their love lives was deeply connected to her passion for supporting and empowering women.

As she gained experience, she realized that dating was a microcosm of broader societal issues, particularly how single women are often undervalued compared to their coupled counterparts. “Dating wasn’t frivolous. It was actually important to our well-being,” she asserted.

Lily quickly became the third most successful matchmaker of the 160 at the firm where she worked. But as she grew professionally, she faced her own challenges in the dating world, leading to personal realizations that would ultimately shape her career.

“I was settling again and again,” she admitted, reflecting on how her upbringing in the Deep South, where traditional gender roles were often reinforced, influenced her relationships.

Determined to break free from these patterns, Lily began coaching herself using the skills she now teaches her clients – self-compassion, owning her preferences and prioritizing her well-being. This transformative process not only improved her own love life but also led to the birth of Date Brazen, her coaching business.

“I started feeling great again, and my dating life was feeling free and flirty,” she shared. Today, Lily is not only a successful entrepreneur but a passionate advocate for helping women find fulfilling lives.

Her passion for empowering women is also evident in her writing. Her recently published book, “Thank You, More Please, A feminist guide to breaking dumb dating rules and finding love,” is a culmination of her years of experience as a feminist dating coach and entrepreneur. In it, she provides readers with actionable advice on how to approach dating with confidence, self-compassion and a deep understanding of their own needs and desires.

Reflecting on her time at Millsaps, Lily credits the school with instilling in her the critical thinking skills and perseverance needed to navigate her non-linear career path. “Millsaps taught me how to think in a lot of ways,” she said.

Lily’s success is also a testament to the close-knit, supportive community at Millsaps. She fondly recalls the deep connections she formed with faculty members who encouraged her to forge her own path and think creatively. “Millsaps is a rich ground for figuring out what you want from your life,” she said.

For current Millsaps students, Lily offers this advice: “Think critically about what path you actually want to take that is outside of what was expected of you and your upbringing. Be open to doing it messy,” she advised, emphasizing the importance of exploring and enjoying the process of figuring out what you truly want from life.

Lily’s journey from Millsaps to successful entrepreneur and author is a powerful example of how Millsaps’ collaborative atmosphere, supportive community and focus on critical thinking empower students to pursue their dreams and make a meaningful impact on the world.