5 Reasons Why Dating is Harder This Time Around

“Spill the tea. Why are you single?”

Every single person that has found themselves back in the dating world knows this dreaded question all too well. Whether you’re recently divorced or just got out of a long-term relationship, reentering the dating scene can be stressful and extremely disappointing at first…especially dating after 40.

The game has changed—from new dating expectations to understanding new added layers like “the talking phase,you probably found that it’s been difficult, post-divorce or post-relationship, to find anything substantial—as in a real connection. You’re not alone.

For most people, it all starts with this sense of excitement for something new to do with all of this “new found freedom” and then reality hits and the dating scene becomes a bit monotonous and filled with disappointment after disappointment. It’s no secret that dating is much harder this time around.


Here are 5 reasons why:


  1. Life is different.


Simply put, you have way more responsibilities after 40 and you likely have an entirely different set of priorities than you did in your 20s or early 30s. The challenge that most single men and single women face is having to navigate these different priorities at a different time in their lives, while also trying to incorporate someone else’s life into their own. In your 20s, you most likely prioritized going out with friends and trying new things—you were probably even going out on multiple dates a month. Circumstances have most likely changed since then. You may have children, a more-demanding career, aging parents that you provide for, all of which likely take precedence over making time to date.


  1. Misalignment about expectations.


Listen, when you enter a relationship with expectations that are misguided or unrealistic, I can promise you that you won’t find the happiness you’re looking for. I get it—at this point in your life you know exactly what you don’t want, however the issue lies in whether or not you’re considering your current circumstances and the circumstances of the age group you’re attempting to date. Are these the same relationship expectations you had when you were in your 20s? Which then leads to the dreaded question, “Are you comparing every potential partner to your ex?” At this stage in your life, you can be especially critical based on your own past experiences. Being cautious can turn into being overly critical or extremely picky really quickly. You need to make sure that you give yourself time to understand if you’re actively trying to replace what you had (the good parts anyway) or if you’re actually open to finding something new (that compliments your current lifestyle).


  1. Finding someone that can accept your schedule.


Let’s be real, it’s harder to deal with change when you’re older and all of the compromise that comes with a relationship. Your life is usually more settled at this point and your routine is pretty fixed, so doing new things doesn’t come as easily, like having to compromise with someone you’re actively dating and go over their place for a date instead of staying in the comfort of your own home all the time. People over 40 usually have growing children living at home and their schedule usually revolves around their children. Whether you’re divorced or not or you have kids or not, you may be faced with the question “do I want to be responsible for helping raise someone else’s kids?” should the relationship progress to that level.


  1. Miscommunication about exclusivity.


You could be approaching dating with a bit too much intensity. If you’re in your 40s, you’re likely from a generation that prioritized exclusivity right off the bat—“I like you. You like me. We go together now.” Those days of assuming both parties are exclusively seeing each other because they “hit it off”  for 3 back-to-back dates are long gone. Enter the “talking phase”—where both parties are getting to know each other, which includes phone calls, FaceTime dates, & in-person dates. In most cases, either party can also be “getting to know” other people. In this age of technology, people are very much in a constant state of collecting data from as many people as possible (dating) before they ultimately choose which data they actually want to spend more time analyzing (exclusivity). The key here is communication. Don’t be afraid to ask the hard questions—are you seeing anyone else? Are you interested in being exclusive?


  1. The dating pool is a lot smaller.


More people were single in their 20s at the parties you went to, now everyone is booed up.

The most common way people meet their partners is through friends. As you get older, your friend group usually gets smaller—quality over quantity. This can pose an issue since it reduces the amount of connections you can make now that you’re older. This then leads to people having to try out anxiety-inducing methods like online dating, which can be a breeding ground for miscommunication. New technology just leaves room for misunderstanding—from swiping through potential matches on dating apps to communicating with possible partners via text or DM—so much can get lost in translation. Nothing beats a good old fashion face-to-face conversation.

There is love again after heartbreak—you just have to be open to it and open to navigating the new landscape.

Join Me at Eddie Offline: An Exclusive Single's Social

I was inspired to launchEddie Offlinewhen I found myself back in the dating pool after my divorce. I don’t know about y’all, but meeting someone at a club or bar just ain’t it for me. I wanted to create an environment where I could bring together like-minded individuals and facilitate good conversations and good vibes. Enter “Eddie Offline”—an invite-only, intimate singles social with house party vibes, hosted by yours truly. Does this event match your vibe? Follow the link below to register.



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