How To Start Dating Again: 5 Powerful Tips To Get You Back Out There

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You’ve been out of the game so long, you’re not even sure where to begin. Whether you’ve been married and then divorced or simply were in a long-term relationship that recently ended, it’s understandable that you’d be apprehensive about how to start dating again.

After all, the dating landscape has changed. Significantly.

Where in your 20s, you didn’t worry about much beyond whether he was going to call (on your landline, at that), now you have to deal with online dating, dick pics (yea, they’re real), and textiquette. All that on top of not being entirely sure what you want in a man at this point in your life.

At one point, you were desperately looking for a husband so you could settle down and have the whole 2.5 kids and white picket fence.

Now? You’re not sure you need that anymore. And if you do still want it, you want to ensure you don’t make the same mistakes you made with the last bozo.

It’s scary to get back to dating, for sure. But trust me that once you take that first brave step of getting started, you’ll quickly learn how to start dating again.

It’s like riding a bike. You never really forget what you’re doing. The bike might be electric these days, but you’ve still got the skills. Trust me on that.

How To Start Dating Again Tip #1: Make A List Of What You Are Looking For

list of what you want

Making a list of what you want in a man can bring you clarity.

If you’ve genuinely healed from whatever past pain you suffered in your last relationship and are ready to find love again, start by using your past to shape your future.

You already know what you don’t want in a man (a cheater, liar, or lazy good-for-nothing), so focus on what you do want. Making a list of the qualities and characteristics you want in a boyfriend or partner is an excellent way to get clear on what you’re looking for.

Your list can be as detailed as you want. Hell, it can be as superficial as you want. No one’s going to see it but you.

I want a man who…

is rich.

is funny.

drives a red sports car.

has a big…

You do you, lady. Be honest about the things that are important to you, because that’s what you want to attract.

Editor’s note: Ready to attract love with a proven strategy? Watch this free video to learn the 7 powerful steps

And while you might be tempted to write what you don’t want (I don’t want a man who can’t express himself), it’s been proven that using negative statements produces negative results. There’s a belief with the Law of Attraction that if you say I don’t want a man who can’t express himself, the Universe only hears a man who can’t express himself, and assumes that is what you want.

So try rephrasing it: I want a man who can express himself fully.

Think it’s mumbo-jumbo? Give it a try anyway. What’s the harm in putting what you want in a man out there as you learn how to start dating again?

As you start learning how to start dating again, your list of what you want in a partner may look significantly different than it would have in your 20s, and that’s okay. Here are a few things you might want to include:

  • Whether he should want to get married or not/has been married before
  • Whether he wants kids/has kids
  • Physical appearance
  • Income and education
  • Personality (funny, intelligent, witty)
  • Interests (sports, travel, reading)

Bonus Tip: Keep your list where you can look at it often. As you start to meet men, see how many items they can check off your list of wants. While you might not meet a man with 100% of the items on your list, you can at least keep focused on what you want so that when you meet men that in no way fit what you’re looking for, you can quickly move on.

How To Start Dating Again Tip #2: Get Into The Mindset of Having Fun

I’ve met a lot of women that, as they’re learning how to start dating again, simply get paralyzed at the prospect of getting back out there. The idea of getting on a dating app, meeting someone for coffee, or even texting a man fills them with fear.

Do you feel the same?

Him: So, tell me about yourself.

You: [thinking] Uhhh…what do I say? What does he want to hear? What’s the right thing to say to make him fall in love with me?? AGGG!

Let me just say: dating isn’t a job interview. It’s not the Miss America pageant. You will not be graded.

The man you go out with next does not have to be your life partner. Heck, you don’t even have to go on another date with him if you don’t want.

Dating is supposed to be fun!

Once you can shift your thinking away from it being a stressful chore and toward it being enjoyable, you’ll be able to lighten up and relax. And when you’re relaxed, you’re better able to open up to the guys you meet.

You’ll likely go on a lot of first dates as you look for The One. If your attitude isn’t ugg, not another first date that will end abysmally, you might actually have a good time. At the very least, you get coffee or a meal out of it. And even if you don’t feel romantic sparks, you might find a new friend. Maybe your next date will be your new hiking buddy. Maybe he’ll eventually introduce you to his friend, who you fall for. You just never know.

So don’t set your expectations so high for dating. As you adjust to how to start dating again, be open to dating being another activity you do to be social and have fun.

Bonus Tip: You might get tired of going on the same types of dates over and over again, so take control next time and suggest a fun venue like mini golf, hiking, or a picnic to shake things up and keep things new.

How To Start Dating Again Tip #3: Try Something New

online dating

Give something new like online dating a try.

You might have sworn that you would never ever in 1,000 years try online dating.

Let me ask you: why?

Why would you write off a proven channel for meeting men who are looking for a relationship?

Dating apps aren’t just for people looking to hook up on Tinder. In fact, you might be more likely to find the guy you’re going to marry on an app.

In a study funded by eHarmony and published in the journal Proceedings of the National Academy of Sciences, researchers found that people who had met their spouses online had more satisfying marriages than those who met their spouses offline. There was also less incident of separation or divorce for those who met online.

So what’s the harm in trying it out? Set up a profile, peruse a few men’s profiles, and see what happens. I bet you’ll get a message from a hottie that will get you excited and thinking differently about online dating.

Bonus Tip: Try at least two different dating apps or sites to start with, because they all have slightly different features. Bumble, which allows you to swipe right on guys you’re interested in, lets you make the first move in starting a conversation. OKCupid and Match have large pools of men and more detailed profile data, and either the man or the woman can initiate conversation.

How To Start Dating Again Tip #4: Update Your Routine

couple at gym

Learn to start dating again by updating your routine.

The older you are, the harder it seems to be to meet people. While in some ways that’s true if you have continued the same patterns you’ve always had (go to work, go to store, come home), it doesn’t have to be your reality. The trick is to get into a new routine that will maximize your opportunity to meet potential dates and to see opportunity everywhere.

You might not have considered the gym as being a great place to meet men, but 47% of Americans find that to be true. And just think: it’s one more motivating reason to put on your yoga pants and head there, even if you feel like eating ice cream on the couch.

Singles mixers are another place that can be great for making contacts.

Check to see what events target the demographic of men you’re trying to meet, then grab a single girlfriend (or be brave and go alone) and have a good time. Again, set your expectations low; you may not meet Prince Charming, but you might get your dance on, which you might not have done for years. Be confident, talk to as many people as possible, and don’t be shy about giving your number to that cute guy with the nerdy glasses.

Make being open to meeting someone part of your new routine. If you’ve taken my advice offered on how to start dating again by venturing into online dating, plan to spend 5-10 minutes each day browsing men’s profiles, sending messages, and responding to messages. Schedule at least one singles mixer event a month. Fit more opportunities into your schedule.

Bonus Tip: One great way to invite new opportunities into your life is to start saying yes more. If a friend invites you to a party with people you don’t know, resist your habit of saying no. You never know who you’ll meet. Say yes to trying new things like attending a ball game or kayaking. Even if you don’t meet a man, you will expand your experiences, and that makes for a more well-rounded and therefore attractive woman when you do meet a guy.

How To Start Dating Again Tip #5: Be Optimistic About Love

woman love

Believe in love again.

One of the biggest barriers to adjusting to how to start dating again at 40 (or 30 or whenever) is a mental one. You’ve been hurt before, and your heart wants to protect itself from future pain.

If I date again, I’ll attract the same narcissistic asshole.

I can’t risk being vulnerable again.

If my 17-year marriage wasn’t love, then love doesn’t exist.

Your mind tells yourself all kinds of things to keep you from risking pain again. But you know the saying: no pain, no gain. Look, I can’t promise you that you’ll never get hurt again in love. Probably you will. We all do. But that’s part of it. That’s the price you pay for eventually finding the kind of lasting and beautiful love you have only dreamed of until now.

So believe in love again. Be open to falling madly, deeply into it. Because if you base your opinion about love on the last guy who broke your heart, you’re doing yourself a disservice. He wasn’t love. If he was, it wouldn’t have ended. So yes, you might have wasted years with the wrong man, but now you’ve freed yourself from him and are completely open to finding real, true love.

And this should make you feel better: a study by Kingston University found that women are happier after divorce. They’re no longer settling for a Good Enough relationship. They know they’re worth more than the last man made them feel they were worth. They’re optimistic about love. You can be too.

Bonus Tip: Even if you can’t possibly believe that love is around the corner, pretend that you believe it. Use the “fake it ’til you feel it” strategy to convince yourself that you can find love. Don’t believe that will work? A study way back in the 20th century by Victorian philosopher William James proves otherwise. James had a theory (though, unfortunately, no one really took it seriously until much later) that forcing a smile should make you feel happy, and frowning should make you feel sad.

He further hypothesized that people could create any feeling simply by acting as if they were experiencing that emotion. So go ahead. Prove William James right. Pretend that you believe love will come your way soon and see what happens.

How To Start Dating Again Tip #6: Take Your Time

biking couple

Take your time getting to know him.

One issue I see time and time again with women who are getting back into the dating game is that they rush it. Some may simply want the comfort of being in another relationship quickly and may rush the dating process to get to that familiarity. Others may simply not want to be in the dating pool and may settle for the first guy that looks their way.

What’s your excuse? Why do you want to rush into a relationship?

The first reason I urge you to take your time as you navigate how to start dating again is that you’ll probably need more time than you imagine to heal from the pain you’ve been through if you had a traumatic breakup or divorce. I know that just a few months after the end of one relationship, you can feel like you’re totally ready to move on, but believe me: you might not really be.

What will dating do to you when it reminds you of those unresolved trust issues you thought you were past? Will you come undone the first time you have sex with someone new? Will you be defensive with every guy you date, assuming he’ll break your heart like the last one?

And even if you have fully healed from past relationships (experts say it can take 6 weeks for a shorter relationship, and months or even years for a long marriage), there’s still plenty of reason to take things slow when first getting to know a new man.

Think about how long it took you to really know your past partner. It might have been a year or more before you knew every quirky thing about him. Every fear. All his past stories. When you learn how to start dating again, the first thing you might realize is: wow, I don’t know this guy at all. You’ve got to start that getting-to-know-you process all over again.

And that takes time.

But take it from me: there’s something completely beautiful about the process of getting to know someone and in falling in love. So go slow. Don’t rush it. Savor every last minute of it. Because if this particular guy is the one, you’ll one day look back and remember these early days fondly. Even if you’re going on dates with multiple people, take your time and enjoy the single life. One day you won’t be single, and you want your memories of this period of your life to be pleasant.

Bonus Tip: If you get frustrated with dating, take a break in between. It’s perfectly okay to have some “you time” in between where you aren’t focused on finding someone to quell your loneliness. Because in truth, you have to be okay being alone before you can be a good partner to someone else.

How To Start Dating Again Tip #7: Accept That Some Things are Different

dating online

Be open to new ways of dating.

There’s no question that dating in your 40s is a different animal than it was in your 20s. You’ll need to adjust to meeting men through mobile apps and websites. You’ll need to step up your texting game. You’ll learn all about things like ghosting and sidebarring. But those are all superficial changes that you’ll adapt to as you learn how to start dating again. Realize that the fundamentals of who you are as a woman seeking a man are probably the same as they ever were.

Standards and personality don’t change that much over time.

If you were unable to date more than one guy at a time in your 20s, you’re probably not suddenly going to be able to develop the knack for doing so now. If you could never have a one-night stand back then, trying to have one now will probably be something you end up regretting. So stay true to who you were and who you are. Be willing to try new things like online dating, and to adapting to the new way of dating and finding a relationship. It may be uncomfortable at first, but in the long run, I guarantee you’re going to have fun.

Bonus Tip: You don’t have to become an overnight dating expert. Take one thing at a time and master it. So maybe your first stop is learning how to send flirty texts. Spend some time gaining confidence in that area before moving on to say, online dating.


You may wrestle with the question who am I now that I’m older and dating again, and you may try to be as different as you can be from the young woman who ended up in a relationship that hurt so much.

You are different. You’ve had different experiences — including that negative one — and now that you’re older, you know better what you want.  But there’s still value in being true to who you were then. So allow that former self to shine a little bit, especially if she was sexy and confident. You may fret over not being as thin as you once were, or think that no guy’s going to want you with the wrinkles and gray hair that might be showing up, but you’re wrong.

Many men will jump at the chance to ask you out and to spend time with you. Realize, they’re on the other side of this equation. They worry that a beautiful woman like you won’t be into them because they’re balding or heavy or out of shape. Everything you feel, they feel. Doesn’t that make you feel better?

My best tip for learning how to start dating again is simply to be yourself and enjoy the process. Being fake never helped anyone. You might have tried to be someone you weren’t when you were younger. But you’re older now and know better.

You also know better than to take any shit from any man. If a man you’re dating isn’t giving you exactly what you want, move on. There’s a reason they say there are other fish in the sea. There absolutely are, and as a sexy, confident fisherwoman, you have your choice of fish to catch!

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