Text that reads 'About OSO IN LOVE' with a black background.

Video Production

Big Day Photo + Video Co.

Food + Cake Films, Sydney Clarson LLC

Video Excerpts

Working with the award winning OSO IN LOVE experience is like no other. We are a one stop shop offering a variety of wedding services, making it easy for couples to bundle services.

Centered around empathy and taking great care and concern for your wedding day—we will be your advocate, cheerleader and sounding board.

Beginning with the initial meeting, your wedding curator will guide you along the process and be with you through the event. Consider us your partner, your friend, your family.

Text graphic with the words 'Meet the Team' in white on a black background.

Black and white portrait of a smiling man with glasses, a septum piercing, a beard, and a herringbone flat cap wearing a plaid vest.

The text 'Rob Anderson' in large, stylish black font on a white background.

Known affectionately as Papa Bear, Rob Anderson is the owner and founder of OSO IN LOVE.

As a Certified Wedding and Event Planner, Rob brings a unique combination of musicality, experience, and deep personal connection to every celebration. Identifying as an openly gay male, Rob brings a thoughtful, inclusive, and creative approach to every celebration he curates. His attention to detail and commitment to excellence set the foundation for truly personalized weddings.

Rob has a natural talent for creating calm, joyful, and memorable atmospheres, seamlessly blending his passion for music, storytelling, and personal connection into every wedding. His focus is simple: to ensure that your wedding is as smooth, elegant, and meaningful as possible. Rob can’t wait to bring your vision to life.

Let’s start this journey together.

Owner/Operator

Black and white portrait of a woman with dark, wavy hair styled back, wearing a black top and a delicate necklace, smiling softly

Text reading 'Jenny B.' in dark blue font against a black background.

Wedding Curator

Jenny B. has been a valued member of the OSO IN LOVE team since 2022. She has worked closely with couples on day-of wedding coordination while also supporting Rob with administrative projects and large-scale events.

Jenny’s passion for event planning began during her college years, where she served as the president of two student organizations and coordinated numerous celebrations and performances. During graduate school, she further honed her organizational and planning expertise by assisting with the coordination of national research conferences.

In addition to her role with OSO IN LOVE, Jenny is a research scientist at UW-Madison and serves as a manager for an annual anime convention. She holds a Bachelor of Science in Biochemistry and a PhD in Population Health, both from UW-Madison.

With a deep commitment to helping others feel cared for and a sharp attention to detail, Jenny brings her extensive event experience and logistical expertise to OSO IN LOVE. Her goal is to ensure that every couple can focus on enjoying their special day while she manages the behind-the-scenes details.

Black and white portrait of a woman with curly hair smiling and wearing a necklace and a dark top.

Text that says 'Sarah R.' in large, dark font on a black background.

Sarah R. joined the OSO IN LOVE team in 2024. Sarah is dedicated to celebrating love at weddings. She finds joy in witnessing couples make their vows surrounded by family and friends. She has worked closely with couples on day-of wedding coordination while also supporting Rob with administrative and creative aspects of the business.

When not coordinating weddings with OSO IN LOVE, Sarah loves checking out local coffee spots, dancing, supporting those around her, and spreading positivity like a true cheerleader! She attended UW-Madison for International Studies.

With a creative and caring energy, Sarah has an innate ability to make others feel at ease. Sarah’s approachability and witty sense of humor have been a welcome addition to OSO IN LOVE. Her goal is to put every couple at ease and manage all details for the wedding so that the couple can live in the moment on their special day.

Wedding Curator

Kyley joins the OSO IN LOVE team with over seven years of comprehensive, hands-on experience in the events industry. Her diverse background—spanning catering, guest services, and same-day coordination—gives her a unique, 360-degree understanding of what it takes to execute a flawless celebration. A lifelong learner, Kyley earned her Wedding & Event Planning certification in 2024 and graduated from Madison Area Technical College in 2025 with a degree in Business Management and Administration, blending creative passion with strong logistical expertise.

Kyley is deeply inspired by the rich traditions and heartfelt emotions that make every wedding unique. She finds her greatest fulfillment in the meticulous behind-the-scenes work, ensuring that every meaningful detail comes together to create a seamless experience for couples and their guests. When she isn't bringing wedding dreams to life, Kyley treasures time with her fiancé and two children, exploring new activities together. She is also a dedicated member of the local professional community, frequently attending networking events with Women of 608 and the Wedding Industry Network to stay at the forefront of industry trends.

Wedding Curator

Trent joined the OSO IN LOVE team in 2026, though his connection with founder Rob and the brand began well before then. As one of OSO IN LOVE’s clients, Trent worked closely with Rob to plan his own wedding in July 2025. Through that experience, he was inspired by OSO’s mission to create celebrations that are both beautifully designed and rooted in the genuine love shared between two people.

Coming from a professional background in journalism with an emphasis on visual media, Trent brings a strong eye for detail and a natural sense of storytelling to his work. His thoughtful, intentional approach will help couples bring their vision, values, and personal style to life while ensuring every element of their wedding comes together seamlessly.

In addition to his role at OSO IN LOVE, Trent is a manager at a local garden center in Madison. Outside of work, he enjoys gardening, hiking, and camping with his partner, along with spending time with their two adorable corgis, Banjo and Charlie — so don’t hesitate to say hello if you see them out for a walk.