6 things to consider if you’re thinking of dating someone (a lot) older


By Sanjeeva Suresh

6 things to consider if you’re thinking of dating someone (a lot) older

How many times have you looked up from your computer screen, saw a pending deadline, and thought, “I can’t wait to marry someone rich, live a life of leisure and not worry about work”? Dating someone vastly older used to be regarded as a taboo. The slang terms “cradle-snatcher” or “gold digger” are often associated with such relationships’ social stigma.

However, things have changed, and Hollywood may (or may not) have had a part to play in its mainstream acceptance. In the 1957 movie Love in the Afternoon, Audrey Hepburn was three decades younger than her onscreen love interest Gary Cooper. More recently offscreen, Harry Styles made headlines when he was photographed holding hands with Olivia Wilde during a friend’s wedding in California. Even French President Emmanuel Marcon‘s wife Brigitte is 24 years his senior.

While the list of Hollywood couples with large age gaps (George Clooney and Amal Clooney; 17 years, Catherine Zeta-Jones and Michael Douglas; 25 years) goes on and on, the question remains. When it comes to dating someone with a large age gap, is age just a number?

Here are some things you should consider:

1. What do you have in common?

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When you remove the sexual tension and strip away all the “sweet” elements of infatuation, is the relationship strong at its core? Do you have engaging conversations with one another? Do you have similarities and understand each other’s pop culture references? According to a survey conducted by The Independent, the most important trait amongst 2,000 singletons was “meaningful conversation”. The survey noted that good communication was ranked higher than physical attraction, with 60 per cent of participants agreeing that conversation was crucial, especially during the initial dating stages. Laughter is important too. In 2019, the Evening Standard reported that couples who have a shared sense of humour and can laugh at one another are the strongest.

2. Be wary of intentions

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Be frank and upfront with your intentions. Be open to questioning why you are dating this person. Is the only reason he’s into you is that you’re young? Are you purposely seeking someone older because you perceive them to have financial stability? Social media is abuzz with TikTok stars flaunting their paid holidays and extravagant gifts courtesy of their “sugar daddies”. The Dailymail reports that the hashtag “sugarbabies” has racked up over 211.4 million views on TikTok. While the notion of being a “sugar baby” may sound tempting, it isn’t for everyone. In 2018, The Independent interviewed a student “sugar baby” who said she “would feel dirty after even just talking to them (sugar daddies) because they are so horrible, sleazy and arrogant”. Think of it this way: Any relationship where one party uses the other for materialistic reasons (especially sex of money) is already a huge red flag, regardless of an age gap.


3. B is for… boring

The saying goes “you can’t teach an old dog new tricks”. That isn’t always the case, but for the most part, as people get older, they become comfortable with a fixed lifestyle and aren’t always open to going out of their comfort zone. A relationship should have some sense of give and take. According to research, vast age gaps, especially in earlier life stages (e.g. 20-year-old dating a 40-year-old) have more issues than couples with age gaps in later stages of their lives (e.g. a 50-year-old dating a 70-year-old). The research explains that as people get older, their potential issues diminish with age. Picture this, if you are in your mid 20’s, (in a pre-pandemic world) you may have the urge to go out, have a few drinks and stay out on weekends. Someone older may have different priorities.


4. Do a background check

As recent reports on Armie Hammer have shown, all that glitters is not gold. While Hammer’s “cannibalistic tendencies” are only alleged, the accusations against him have caused a dent in his previously charming on- and offscreen persona. If anything, it goes to show just how important it is to be able to spot red flags. More often than not, there is usually a pattern to the behaviour. Be open to communicating any insecurities you may have. If you happen to find out that your partner’s “type” is someone vastly younger, maybe reconsider your options. If you are dating someone older, it’s normal to wonder why your partner has been single up until that point. It is good to have an open discussion.

5. Do you “mind the gap”?

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Are you comfortable meeting each other’s friends and family? Yes, at the end of the day, the relationship is purely between you and your partner. But heaven forbid, the older party gets mistaken for the parent. When problems do arise, it’s important not to blame the age difference and remember that every relationship goes through its own ups and downs, again, regardless of age. Know where your boundaries are.

6. Is there a future together?

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At the end of the day, the age gap doesn’t matter. It all boils down to where you see the relationship going. Will you or your partner be having a wandering eye? The grass always seems greener on the other side. Are you going to have FOMO (fear of missing out) when you see other couples with closer age gaps? One 2016 study found that 74 per cent of women in age-gap relationships felt they were “securely attached”, so perhaps not. It is important to note that every couple has their own set of challenges, but if you picked the right person, you’ll get through it together and make it for the long haul.

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