When it comes to dating, age is just one among many factors to consider as you seek your match. We bring all of our prior life experience to any relationship we enter, so how much does it matter that one person's history is years or decades longer than the other's? Here, two experts weigh in on the benefits of dating an older man, as well as the potential drawbacks. While an older man dating a younger woman tends to raise less eyebrows than a woman's romance with a younger man , the dynamic isn't exactly stigma-free-particularly when the age gap is significant. Three years later, search husbandnotdad on Instagram and you'll find a collection of smiling couples; on Twitter , the same hashtag's happy photos are interspersed with searingly critical comments, which arguably confirms Thornton's point.