Dating Again In Your 50's: A Guide

You’re never too old to enjoy life and put yourself out there. Especially not in your fifties, which in this day and age, is still comparatively young. In fact, going out and enjoying yourself is so much better when you’re middle-aged - you have no need to impress others, to look cool, or to do anything you’re uninterested in. Instead, you know who you are, what you want, and what personalities you prefer to be around.

Put simply, at this age you start to lose many of your illusions and can focus on having a genuinely good time. Moreover, you take more pleasure in the simple things - a comfortable lunch date is just as enjoyable as a night clubbing might have been in your earlier youth.

For this reason, dating again in your fifties, even if it’s been some time since you were last romantically active, can be an inspiring use of your time. With that in mind, you may wish to consider some of the following advice:

Consider More Professional Dating Apps, Platforms, Or In-Person Events

By “professional” we mean those that have been carefully designed to favor good relationships, thoughtful dialogue, and respectful encounters. Yes, there are many “dating apps” out there, but unfortunately many of them are designed to treat others as disposable. It’s healthier to use platforms that offer you a fuller profile of individuals, and of course, some of them are tailored to specific life needs, such as if you require a religious partner.

Yet this is only really applicable if you intend to online date to begin with. While there’s nothing wrong with doing that, opening yourself up to more in-person encounters can encourage you to get out there. For example, heading to local running or craft clubs, taking time to meet friends of friends, and being more social is a good way to challenge yourself. That’s not to say you should get out this way for the sole purpose of romantic interest, only when you become more interested in hobbies and passions, those who share your love are more likely to come across your path.

Don’t Date With Expectation

The great thing about dating in your fifties is that in some respects, you’ve already gathered a good amount of life experience. You may have had marriage or long term relationships in the past, and you may even have children. For this reason, the obligation of doing all this with someone new might not be present.

For this reason, you can enjoy the experience more, as opposed to “what happens” at the end of it all. You’ll live more in the moment. Make sure to capitalize on this, such as by heading to quirky dates you find fun, exploring the tastes and interests of your partner, and not being afraid to enjoy simple activities. If you enjoy their company, all of a sudden an expensive date meant to impress isn’t quite as essential as it once was.

Be Upfront & Unashamed Of Who You Are

When you get to middle age, you also understand that you have nothing to prove to anyone. This can be quite freeing when you’re dating other people. You won’t feel as though you need to hide your nerdier interests, or your political viewpoints (except where bringing them up is tasteful, of course), or your past experiences. Being who you are, without shame, can be helpful.

For example, if you have children, you can say that. If they ask you about the arrangement, you might be paying child support, but you can tell your date that you’re still in contact with the family and make sure to support them. At fifty, everyone has been through good and bad, and so making your own situation clear is healthy. Moreover, if you’re candid, then the other person will no doubt be candid with you.

Then you don’t have to worry about being accepted or not - if you are, then you likely gel well with the person you’re seeing. If you don’t, well, you haven’t lost anything in particular. Understanding that makes the process less about fear and hesitation, but more about fun, learning, and experimentation.

Consider What Your Desires Are

It’s important to be compatible with the person you’re dating in middle age. After all, this is still a transitional period. It might be that you’re dating someone who still wishes for children, but due to your age, that might not be as possible. Or perhaps it could be. The dividing lines are not always so clear.

Or, maybe you’ve been married twice before, and you’d rather not marry again. That may change after ten years with the right person, but making your current intentions clear is respectful and the right way to go about things.

As before, being clear about your interests and intent for the future can help you avoid stringing someone along, or wasting their time. At this time in life, everyone has different wishes. Maybe they’re looking for a romantic partner as well as a potential stepparent to their children. If you’re unwilling to fulfill that role, it’s important to be clear about it. But remember that you can’t pick and choose what parts of someone you become involved in, if you expect them to accept you wholeheartedly, you must do the same for them too.

Bonus: Genuinely Go With The Flow

You don’t have to achieve anything when dating in your fifties. This means you can enjoy yourself more than anything else. If you have a nice dinner booked with someone lovely, that’s a win, even if it leads to nothing. Keeping this open mind allows you to avoid feeling overly strict about your time, which some people can at this age. It also means if anything natural develops, it will have done so without you forcing it.

With this advice, you’ll be certain to date again in your fifties, or at any time in your middle age. We’re willing to bet that if you give it a chance, you’ll even prefer this to dating in your earlier youth.