A decade ago, when Mandy Ginsberg asked couples how they met, some would give a fictitious answer: “Oh, we met through friends.” When she then revealed she worked at an online dating company, their answers shifted: “Oh, we actually met through Match,” they told her.

In her nearly 13 years at Match Group Inc., where she became chief executive in January, Ms. Ginsberg has watched the stigma of online dating fade almost entirely. Today, many people even proudly pursue a multiapp dating strategy.

Match...