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5 Rules for Dating After 55

DETANGLE’s Insight


It can be quite hard to get back into dating after being in a committed relationship for years. It has been hard for me too after a long marriage, but I made some rules for myself whenever I went out on a date. Sure, these rules aren’t everything, but they can help you stay composed even when you are nervous. I know they worked for me, so give them a read; they may just work wonders for you too!

Did you know there are some simple rules you could follow if you want to successfully get back into the dating game after 55?

It isn’t easy to go back into dating after you have been committed to someone for a while, or if you have not done it in a while. And while there are no concrete rules about what you can and cannot do for everything to go perfectly, you should have some rules that you follow in order to make sure that you have the biggest chance of success.

After all, we are all going into these dates hoping to find another partner with whom to share our lives and be happy. Dating after 55 means you are taking back control of your love life, just as you have done with other areas of your life, and it doesn’t have to be daunting. Yet, it is very different from dating when you are a young adult; certain things have changed, and some things do not fly anymore now that you have matured.

To ease the change that you go through when you decide to start dating again as a mature adult, we have gathered some of the best rules you should keep in mind so that you can have the best experience. Be it about things you should do or things you should definitely keep an eye out for, these five rules will take you a long way!

Let us know if you have used any of them in the comments!

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Photo by Jacob Lund House at Shutterstock

Be careful with the conversation and make the most of it!

Conversations can be tricky, especially when you just start dating again, but you have to be able to navigate any situation like a pro and keep tabs on how the discussion is going. The rule is that if you feel like you haven’t had the chance to say a word, or learn about them, or if they have been talking way too much and only about themselves, you should probably not count on a second date. If anything, you should lower your expectations right away: you deserve someone who is willing to share aspects of themselves while also wanting to learn about you.

Do not settle for boring conversations, and never allow an uncomfortable topic to linger too much. The point is not to have difficult talks but rather to discover things about one another during your first few dates. You are already charming and amazing, so as long as you come to the date open and ready to have a good time, you should be able to inspire the same in your date as well.

And if that is not the case, do not worry! There are more fish in the pond, and even a date that did not go as planned can teach you a lot!

Remember, this is not college anymore!

Yes, we mean that, even if it sounds like a silly rule. Flirting as an older adult is very different from flirting as a young adult. Not only are you looking for different things, but you have already found your likes and dislikes and where you draw a hard line. You cannot be the same bashful, shy kid on a first date.

During a first date, the rule should be to keep your body language as open as possible, be flirty but not come on too much, allow yourself to smile and laugh, and if the situation is appropriate, do not be afraid to touch their arm. Do not shy away from compliments, and make the most of your charisma and charm! There’s no reason to hide that charismatic, playful side of you. Put your best self forward and flirt in a mature way.

They’re going to love that!

Never rush into things!

Do you want to forget about those embarrassing moments in your twenties when you awoke the next day and realized what you had done? We didn’t think so either. It is better to not rush into getting physical with your new partner, no matter how attractive you may find them. After all, you are both mature, competent, and smart adults, and while having fun may be fun from time to time, if you intend to have a serious relationship, this is one of the rules to follow to a T.

A lot of people over the age of 50 and even seniors who start dating again agree that rushing into intimacy was something they regretted. And a lot of the time, those relationships did not last as long as they would have wanted them to, or they remained purely physical. This doesn’t mean that you should wait until you are married in order to get intimate; after all, you are all adults, but not jumping the gun is definitely the way to go.

A good way to make sure this rule applies is to ask yourself if you are ready to talk to your new partner about your relationship status, other intimate details, and safe practices. If the answer is no, then you should definitely not commit to being intimate. If the answer is yes, this is your cue to talk to them before doing anything: it’s better to know each other’s likes and dislikes, as well as other important details.

And if they are not on board, good riddance! It means they are not mature enough!

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Photo by Andrey_Popov from Shutterstock

Keep the baggage away!

Since we are all older, we all come to the dating scene with our own emotional baggage, and this can sometimes be a detriment. After all, no matter how your previous relationship ended, you can never know if the person with whom you are going on a date will have the same issues. The conversation is bound to come to the topic of what happened with your previous relationships, but this is where you should be the most cautious!

The biggest rule of thumb is to not bond based on your common emotional baggage! Since the conversation will steer towards this, it is normal to share a few things, but do not let the discussion just veer towards a never-ending discussion about ex-spouses and other failed dates. It may seem like a good way to bond, but it does nothing but share baggage, and you could even be trauma-dumping on the other person.

If this is why you end up getting closer, you can imagine that nothing built on gossip and emotional baggage is going to last or bloom in a healthy relationship. Believe us, staying away from such conversations at the start of your courtship is the best choice!

Try to find out things about the other person!

You should always be in discovery mode when you are first going on dates. After all, it is the best way to make sure you are getting to know the other person. You are no longer in your twenties, and getting to form new connections can be intimidating, which is why you should be positive and open, but also gather all the information you may need to get a good read on your potential future partner.

It may sound like a silly rule, but details count even more once you are over 50 and dating! How they dress, the way they smile (is it a genuine one? ), how they act in public and with the staff of the restaurant, how they speak about their kids (if they have any), ex-spouses, family, and friends are just some of the things that could give you more hints about how they truly are as a person. In the end, both of you will try to make a good impression, so you have to be able to read context clues and read between the lines.

That way, you can easily figure out if the second, third, or even fourth date is worth pursuing! You cannot find out everything in one date and rules aren’t always 100% fit for all situations, but some red flags are there from the first one!

And if they are not acting well, before you tell them it’s not going to work between you two, I recommend you tell them to read this book!

If you’re already in a committed relationship and you are afraid that you may lose that spark during retirement, do not worry! Here are our foolproof ways in which you can keep that fire alive with no problem!

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