Are You Afraid To Date Again? 7 Strategies For Getting Back Out There

“Hi Orna and Matthew,

I have not been in a real relationship in over 20 years and I’m really afraid to date again.

My personality takes a while to unfold with new people (I’m an introvert), so in today’s speed dating kind of world, I feel quite lost and afraid to get out there.

I’ve had a few coffee dates that don’t go anywhere and based on my past history, I don’t really trust myself to meet anyone decent anyway.  How do I get the confidence to even try? I find it’s just easier to be happy with me & my cats.


Tami, the middle-aged crazy cat lady ;)”

Hello Tami,

Thanks for sharing that you’re afraid to date again. Dating can feel like a big risk, and when you haven’t done it in a while it makes sense that you don’t know where to begin to put yourself out there again.

We often hear that the problem is “the way dating works today.” Younger people blame the hook-up culture; others blame dating apps and the Internet. You’re seeing the problem as “today’s speed dating kind of world.”

While technology has changed the way we meet people, what happens when we actually meet hasn’t changed in many decades: Two people share food and/or drinks and get to know each other. If they both agree, a second date follows to continue the dating process. It’s basically the same as it’s been for decades.

Perhaps It’s Your Dating Strategies That Need A Tune-Up?

Most people don’t learn how to date, and if they do anything at all they focus on their outer appearance or their behavior. There are plenty of dating coaches who share the supposed best color dress to wear or how to behave so that you get a second date.

Certainly, when going to meet someone for the first time it’s appropriate to look your best and put some effort in, however, if you’ve been struggling to create lasting love the issue is unlikely to be how you wear your hair, or whether you’re asking the right questions of your date.

Is it easier to just be happy with your life as it is? Of course! Is that what you really want? We would guess not, especially since you wrote in asking for our advice.

If you are afraid to date again, finding a compelling reason to overcome your fear will give you the motivation you need. We know you don’t want to just spend your life taking care of your cats and watching Netflix. You want to find your soulmate and create a life together.

This big goal can feel out of reach when you haven’t dated for several years or even a couple of decades. Instead, focus on small steps along the way to develop your confidence and stretch yourself into new strategies to put yourself out there.



Afraid To Date Again? 7 Strategies For Getting Back Out There

It’s easy to find reasons for keeping things the same in your life, especially when you feel afraid to date again. It’s common for singles to share their dating horror stories and make it sound like there are no decent people looking for a real connection anymore.

That is far from the truth and is one of the biggest reasons you’re feeling stuck and not meeting new people.

  1. Look For Reasons To Say Yes

Don’t try to filter through profiles looking for your soulmate, because you won’t find your beloved in a profile.

You’ll find your soulmate by meeting lots of new people and discovering more about yourself along the way.

Instead of looking for reasons to reject someone (you’ll always find something), look for reasons to say yes to a first meet. You’re not committing to spending your life with someone simply because you agreed to meet him for coffee or a cocktail.

You’ll have a much more positive outlook on the number of prospects available to you when you look for reasons to say “Yes,” instead of rejecting someone because they’re not great at writing an online profile or perhaps didn’t take the best photo ever.

You’ll also begin to move through the world with more open and positive energy, which is in and of itself attractive.

  1. Approach Your Dates With Curiosity

Another way to take the pressure off of a first meet is to reset your expectations. Instead of fantasizing and hoping that this person will be “The One,” approach your first dates with curiosity simply to get to know someone new.

This will help you take the focus off of yourself and allow you to be less self-conscious. Ask questions. Be curious about who this stranger is. Being interested in the other person is also naturally attractive.

Most people like to talk about themselves and feel drawn to people who want to know more about them.

Shifting your focus away from yourself will also take the pressure off of your concern about making a good impression.

  1. Don’t Put Your Lovability In The Hands Of A Stranger

One of the reasons you are afraid to date again is that you are afraid of rejection. Putting all of your hopes and dreams in this other person gives them the power to determine your lovability.

On a first meet, you are dealing with a stranger. He doesn’t know who you are or what really makes you tick.

Why would you give a stranger the power to reject or accept you?

He hasn’t even had a chance to get to know you! As you said above, it takes time for you to open up.

Stop looking for acceptance or love in the eyes of a stranger, that is only setting you up for disappointment. There are people in your life who know you, and these people love you and accept you as is! It’s time for you to bestow yourself with this same grace.

  1. Discover What You Can Learn About Yourself

Use dating as a tool to discover more about your patterns, your limiting beliefs, and your strategies for love. Most people use the same strategies for dating that they learned as a teenager regardless of how many decades have gone by.

Stop dating like a teenager and approach love like the mature adult that you are now.

This means that you can use dating as a tool to learn more about yourself and discover if there are new strategies you want to develop. If you are afraid to date again, understanding your inner dialog will help you overcome your fear.

Notice your inner dialog when you are on a date with someone you are attracted to versus someone you don’t find attractive. Are you more comfortable speaking up when there is no attraction? What strategies show up when you are hot for the guy across the table that you’ve just met?

Pay attention to how you feel immediately after you part from your date.

Do you criticize yourself, thinking about all the things you should have done differently?

Do you easily find fault with your date and see that as evidence that there are no good men out there?

Do you excuse bad behavior and ignore red flags when you feel the intoxication of chemistry?

Discovering your strategies that have caused heartbreak in the past will give you the confidence that you won’t continue to make the same mistakes moving forward.



  1. Share Your Dreams And Goals, Not Your Horror Stories

Many people like to bond over negativity. The saying, “Misery loves company,” is certainly true in the dating world. Resist the temptation to complain about all the nuts you’ve met online and do not share your horror stories no matter how entertaining they may be. Save those stories for your friends.

Bonding over negativity is not a strong basis for a relationship and may skew your view of the guy who is funny, but who can never ever be sincere about anything. It also keeps your focus on feeling afraid to date again.

Instead, share your dreams and goals with your date. Share what you want from life. Ask your date what inspires him and his worldview.

Having similar goals is what bonds groups of people together all over the world. This occurs in business, sporting events, and even families. By sharing your dreams and goals and asking about what inspires your date, you begin a relationship on a positive note and leave the opportunity to connect over the life you would each like to create.

Energy is contagious whether it is positive or negative. On a date focus on the positive, and see if you can inspire your date to do the same.

  1. Practice Being Authentic To Create Connection

Everyone wants to be loved for who they really are, and yet on some level, we are all a bit terrified to show up as who we really are. It is all too common to twist into a pretzel to try to be someone that we imagine the other person will like instead of just being ourselves and letting the chips fall where they may.

Use dating as an opportunity to practice authenticity and show up as the real authentic you. This doesn’t give you a green light to share all of your troubles and struggles with a stranger, it simply means that if you disagree with your date speak up!

Being authentic means speaking how you feel with your date. Authenticity is a high vibration and is an invitation for the other person to meet you there. If your date chooses to meet you there, then you have the opportunity to create a real connection with this new person you’ve just met.

If your date is unable to accept your invitation, then that is priceless information about this person you are just now getting to know. Perhaps he was incapable of joining you in being authentic in that moment but will circle back to connect with you and clean things up.

Showing up authentically while dating gives you three huge benefits:

  • Creating an opportunity to connect with your date.
  • Practice the skills to turn a conflict into a deeper connection.
  • Doesn’t waste your time with people who don’t get you.
  1. Ask For What You Want

Your soulmate doesn’t come with mind-reading powers. He doesn’t instinctively know whether or not you’d like him to open the car door or to bring you flowers.

Do not be afraid to make requests of your dates. You’ll be more likely to get what you want, and you’ll also discover over time if the two of you have shared values.

Beware of thoughts like, “A gentleman would hold the door open for me. He didn’t hold the door so he must not be my soulmate because I want to be with a gentleman.”

Many, many men have received a negative reaction simply by holding a door open for a woman. Making assumptions about behavior can lead you astray and put an unrealistic expectation on this person who could be an ideal mate for you.

Dating is confusing in our modern world. Women want to be equal and they want men to treat them like a lady. Most men have backed off and are waiting for cues from you about what you do and don’t like.

Let him know how to win with you. If he wants a relationship with you he will make an effort to please you and to win your heart.



Instead of focusing on being afraid to date again, use these strategies to help you gain confidence in yourself. They will also help you cultivate discernment through the dating process so you can identify an ideal match for you.

Getting to the root of your lack of trust in yourself and transforming this limiting belief would put your search for love on jet fuel.

Confidence is not something you can paste over your fears so that you can show up and behave differently. Confidence comes when you risk in order to create a new experience. Once you have new positive experiences you’ll gain more and more confidence in yourself and you’ll be more and more open to going on dates and meeting new people.

Dating doesn’t have to be hard, nor does it need to seem like a chore. Approaching dating with an open and curious mindset will give you the right approach to finding your soulmate.

If you’re ready to take your dating to the next level and create the lasting love you really want, download our special report, “7 Steps To Soulmating™.” You’ll receive our top dating strategies that have helped thousands to change their love patterns and finally create their soulmate relationship.

About the authors

Love Coaches Orna and Matthew Walters

Orna and Matthew Walters are soulmate coaches and prolific writers about love. Finding love, keeping love, healing from heartbreak, bringing in your beloved and more. They have been published on MSN, Yahoo!, YourTango, Redbook, and have been featured guest experts on BRAVO’s THE MILLIONAIRE MATCHMAKER with Patti Stanger, and as guests with Esther Perel speaking about love and intimacy.

Suggested Reading