Bill Belichick, 73, the former general manager of the New England Patriots, has been turning heads in recent days for his relationship with the former Bridgewater State University cheerleader, Jordan Hudson, 24, as more new details emerge about their relationship. This includes a sizeable real estate portfolio in Hudson’s name.
Though the story of the hour, May-December romances, romantic relationships between a younger (May) and older (December) person, are nothing new. Cher, Leonardo DiCaprio, and Robert De Niro have all been in relationships with much younger partners. But do they work?
Though there’s the argument that the heart wants what the heart wants, like any relationship, a May-December romance won’t always be sunshine and roses. Far from it. May-December relationships can present unique challenges due to the significant age gap involved — challenges you should be prepared for should you decide to pursue this option. They follow.
You are at different life stages.
It doesn’t have to be as pronounced as the age gap between Belichick and Hudson to have an impact; if you and your partner are at different stages of life and have different goals around career and family, it can present issues in your relationship.
Consider the following: One of you is recently divorced after being a stay-at-home parent and is trying to restart your career at midlife, not just for the money but because you are excited about the prospect of it. Your partner, however, has worked for decades and sees retirement on the horizon, presenting a chance to exit the rat race and travel more often. Or you are the parent of two adult children, while your partner is looking to start a family.
In either scenario, a compromise may be necessary. But ask yourself: Do you want to be the reason why your partner has denied themselves something this important, or the person doing the compromising? Will either of you come to regret it later? These are the types of questions, among others, that you’ll need to answer before going further together.
You and your partner will miss cultural references due to generational gaps.
Perhaps not as significant as changing your life plans based on the stage of life you’re at, but lack of knowledge about music, slang, tech, and societal norms, such as views on relationship status, can, at a minimum, make for some awkward moments. Over time, it can lead to a divide.
Part of being in a relationship is not only having things to talk about but also relating. A knowing glance or a chuckle can be one of the ties that bind two people. When you constantly have to explain something, no matter how kind the tone is used and how well-intentioned it is, it can cause feelings of loneliness and isolation. This is especially pronounced when each partner’s friends in group settings miss the same references.
Family, friends, and onlookers may judge.
Even if you’re not a celebrity or notable figure, friends, family, or the onlooker at the grocery store may criticize, question, or offer a look of disapproval about your relationship. Whether it’s to doubt the legitimacy of the love you share or either of your motives for being in the relationship, hearing the commentary from others can sting. Live in the public eye, the chatter can become exponentially louder.
There can be an inherent power imbalance due to age and experience.
Differences in financial status, life experience, or confidence can create subtle or overt questions of control, specifically about who’s running the show. Go back to Belichick and Hudson, for a moment: Hudson is coming under fire for reportedly interrupting a recent interview to dictate which questions they would and would not answer, leading to speculation about why.
Whatever the case may be for this happy couple, age doesn’t necessarily imply that the older person is in control. This is especially true when cognitive function comes into question, as it did in the dynamic between the late model Anna Nicole Smith and her much older spouse.
Long-term planning can be complicated.
Though no one likes thinking about how much time they have left, and there’s no guarantee as to how long someone will live, life expectancy is what it is. It’s no secret that as we grow older, health challenges, including mobility, become more of a concern. So does cognitive decline.
In light of the above factors, conversations around conceiving and raising children can become complicated. So may discussions about maintaining independence, including whether a younger person fully understands what they might be signing on for in terms of long-term care when choosing to date someone much older.
Final thoughts …
In the end, May-December relationships can bring warmth and wisdom, but they can also cast long shadows if the mismatches that are present aren’t addressed. Like the seasons they’re named for, these pairings can be calm — or they can be stormy when expectations don’t align. If you're considering one, go in with eyes open and both feet firmly planted in the reality that although we are not eternal, the love we share is.