What to Remember When Dating as an Older Single Person

Dating is hard for everyone, and it can feel doubly so if you’re dating as an older single. It can feel like everyone else around you is already spoken for, and like the advice and resources around you are designed for 22-year-olds who live most of their lives on social media. But while dating later in life may have some unique challenges, it can also be a rich and rewarding process that offers fulfilling connections and a space for genuine excitement and fun. Here’s what I recommend folks dating later in life keep in mind.

You aren’t alone, and you aren’t doing anything wrong


In a culture that often suggests to us a very rigid narrative about a timeline for partnership — we meet our One True Love young, marry, and settle down forever to age into sexless parents and then adorable, asexual grandparents. Of course, this narrative is the reality for very few of us — the US divorce rate is between 40% and 50% at any given time, and as many as 40% of new marriages are second marriages for at least one partner. Almost 40% of US adults between 25 and 54 are living without a spouse or partner.

One of the easiest myths to convince ourselves of in dating — and maybe in life — is that everyone else has everything figured out, and we’re the only ones fumbling or feeling like a failure. It’s easy to imagine that you may be the only older adult in your community who’s trying to date, and the dating pool includes only you and five thousand 23-year-olds. In reality, you’re in good company — you have a lot of options in dating, and also a lot of people just in the same boat as you. You’re allowed to feel uncertain or less than enthusiastic about dating, but you shouldn’t feel self-conscious.

Times may have changed, but the important stuff about dating remains the same


It’s completely understandable to feel intimidated stepping onto the dating scene right now, especially if you’ve been “off the market” for any reason for a while. It may feel like there are new terms and expectations that aren’t familiar to you; you’re retired and/or work remotely now, and so you feel cut off from making organic connections with potential dates at work or school; it may feel like the only way to date these days is through an app.

Some of these concerns may indeed crop up; you may feel like there’s a learning curve, or make some new adjustments. It may end up being true for you that you get more dates you want to go on by finding a dating app for 30+ or 50+ folks; it could be that someone expects you to understand or identify with a whole set of terminology you don’t relate to at all. 

However, many of these fears are rooted in something deeper that we aren’t articulating: that dating and relationships themselves have fundamentally changed in ways we aren’t prepared for, and that the type of relationship we want just doesn’t exist anymore — or that if it does, we won’t be able to find it, because dating is a functionally different process now. 

These fears, I can assert with confidence, aren’t true. While the trends and technology around dating are in constant flux, they’re just window-dressing. The core of how dating really works has remained the same: defining your values and what you want in a relationship, and putting yourself out there again and again until you find the person who’s a good fit for both. Knowing how to sext is fun, but isn’t what matters; being clear with yourself about what you want and how you’ll know when you find it is.

You’re free to decide what you really want


Whether they know it or not, many young people are heavily influenced by the idea of a relationship that fits into a specific life path, and finding “the one” who will finally make their life complete. Even though many young people have decided they want something other than a cookie-cutter marriage and kids with a white picket fence, the cultural narratives around settling down or being “chosen” by a certain age are still very potent.

Of course, love, companionship, and stability can be important to us at any age, and it’s completely reasonable to be looking for a partner to settle down with or who’s interested in co-parenting no matter what stage of life you’re in. But many people approach dating a little differently after becoming established in life: we already have our own interests, passions, careers, and home life, and aren’t necessarily looking to dating or a relationship to help us build a foundation for those things. Some of us may be divorced or widowed, changing the stakes on concerns about finding “the one” This frees up more mature people to think outside the box about what they want, and what a relationship could mean to them.

Thinking about your life in its fullness, what are you looking for a partnership to provide? Where would a relationship enhance your life, and where is your life already set up the way you like it? Maybe you realize you’re interested in a relationship for date nights, romantic vacations, and lazy weekends in bed together, but are otherwise enjoying having an empty nest and living alone; you don’t actually want a live-in partner. Maybe your pride at raising your kids as a single parent is important to you, and you want to date someone your kids approve of, but don’t want them to co-parent; you’re looking for a partner, but not a stepparent. Alternatively, maybe your life didn’t lead to having kids at an earlier time, but you’ve always wanted to be a parent; dating could be a way that you find not just a partner, but a family.

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