Date Brazen

Date Brazen is a feminist dating and coaching brand led by Lily, a former matchmaker who supports late bloomers ready to pursue love with confidence and on their own terms. It challenges dating advice that encourages people to shrink, settle, or wait, offering practical guidance to help clients move past self-doubt and build a joyful, fulfilling dating life. The brand reports having helped more than 400 late bloomers.

Its offerings include a 12-month group coaching program focused on dating confidently and attracting a suitable relationship, and Main Character Era, a six-month small-group experience for feminists seeking change in love, friendships, and work. Participants in that program take on 100 audacious, self-directed dares in 100 days. Date Brazen also offers live coaching sessions, actionable dating strategies, a free three-day flirting challenge, and the podcast Late Bloomer, featuring advice and coaching conversations. Lily’s book, Thank You, More Please, combines personal stories, client case studies, and exercises to help readers apply feminist dating principles.