Lolita. Harold and Maude. American Pie. Marked age differences in a romance are nothing new to the world of literature and film. However, are they really conducive to modern-day relationships? Can two people of differing generations find a connection that transcends the decades?

Younger Man + Older Woman Or Older Man + Younger Woman?

The first aspect to consider is the genders as they relate to the ages. Would an older man/younger woman combination be more likely to succeed than an older woman/younger man relationship? Not necessarily, but it is more acceptable by society’s standards. Nowadays, a young woman on the arm of her older partner would not cause one to even bat an eyelash. The stigma of an older woman courting a young man is slowly dissipating, but the situation is still likely to draw jokes about her being a “cougar.” Because of that stigma, it is often harder to be taken seriously as a legitimate couple.

Spring-Time Perks

One of the best ways to succeed in a May-to-December romance is to find a way of bridging the gap. For instance, if you are a young woman (or man) with no interest in the wild dating scene, you may be looking for someone to settle down with right away. Meanwhile, an older man (or woman) has focused on his/her career for most of their adult life, and now they are ready to start a family. These people are able to meet halfway to fulfill their common goals or desires.

Cold Weather Drawbacks

The relationships that seem doomed to fail are the ones in which the couple does not have a connection deeper than appearances, money, or other superficial perks. For example, an older man may proudly find himself the target of his friends’ jealousy when he starts dating a hot 18-year-old. However, the disappointments quickly pile up when he realizes what may accompany this particular age: no previous adult relationships, insecurity, partying lifestyle, and little “real world” experience. Also, you may enjoy the vigor of your younger lover. Yet, what happens if you are ready to have a baby or to move to the countryside, but your energetic partner isn’t ready to settle down?

And Over Time?

Moreover, generations have widely varying ideals, values, and goals from the next. One woman, whose parents are 20 years apart in age, shared her experiences. While the age difference didn’t matter when they were in their 30s and 50s, respectively, it certainly made an impact when they hit their 60s and 80s. When she was younger, the mother hadn’t minded her husband’s old-fashioned views about “a woman’s duties,” such as rearing the kids, cooking, and cleaning. Yet as an aging woman, she no longer had the energy to do all the housework. Also, as he grew older, he became less interested in such activities as traveling—even though she was still into traveling the world.

“While a big age difference is irrelevant for a time,” she concluded, “it’s almost guaranteed to cause problems if you’re still together when the older person is actually old. They have a good relationship despite their differences, though. They knew what they were getting into and decided they loved each other enough that they’d deal with it.”