6 Dating Tips for When You’re Getting Back Out There

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After a heart break, (or heck, maybe not even after a heart break) it might take you days, weeks, months, sometimes ever years, to gather up the energy it takes to date. You download that dating app once more, there’s a brief thrill of new love and possibility. You swipe, you match, you start those awkward conversations…sometimes leading to connection and exchanging numbers, sometimes its crickets and sometimes it leads to “wow, I can’t believe that person said that…UNMATCH.”

You decide to meet up in person or do a video date and before you walk into that restaurant or click that zoom link, you take a deep breath (or at least I do) and pray that it goes “okay”. Sometimes you get so nervous you can’t even get your words out and other times you know the moment you meet them that its not your person.

Putting yourself out there is a big risk, not only for meeting someone and it going horribly wrong, but it could also go horribly right. Will you be able to trust yourself? Will you see red flags? Will you be confident and set boundaries? Will you be charming and funny enough? So when you think about it, its really quite marvelous that that we all put ourselves through it, over and over again, just for the chance that maybe, just maybe that it will work out and you’ll meet someone. I mean, are we all insane?

I’ve also come to realize that the prospect of finding someone it could actually work with is almost just as terrifying as going on a date with someone you have no chemistry with. At least in that case you can move on, but if you end up really liking someone, that means you are opening yourself to possibly get hurt again. You’ve got to let go of all the other things (and people…ghosts) taking up real estate in your heart. You’ve got to create space. And am I ready to do that? Because if I fall in love with someone new, I have to let go of all my “what if’s”. And maybe that’s what’s so beautiful about new love. Laying down your past and deciding to walk forward with someone, not knowing what’s going to happen next.

Here are some important things I’ve learned on my dating journey:

Figure Out Why You’re Dating

Do you have a goal or a purpose for dating? Are you dating because you truly having something to give? Or are you lonely? Are you still sad or stuck in past hurt? Are you bubbling over with joy and ready for possibility? Where are you emotionally right now? Is your energy heavy and tired or light and fun? Are you already whole or are you looking for someone to complete something you think you are missing? Its okay to be in all or any of these places, but be aware of what you are putting out there because it does affect who and what you’ll attract.

Decide What You Want First

If you are looking for something serious, be honest about that. Don’t pursue someone that says that are only looking for something causal. That will always lead to disappointment. Likewise, if you are looking for something casual, communicate that and don’t give someone false hope. Let them know if you are dating other people or if you are a one person at a time kind of person. Also, there is nothing wrong with being in either place! Its all good, as long as you are upfront and on the same page as your partner/s. And please, please talk about these things before having sex. What you or your partner wants should never be a surprise.

Its Okay If Its Not a Match

If at any point while getting to know someone you realize you don’t want to move forward, its okay! Be kind and let them know! You don’t have to give them counseling or feedback on why you didn’t match, but don’t ghost and be honest! And if they react negatively to your honesty, well then that’s confirmation that you did the right thing. If they say they can or want to change to be what you want, also, big red flag! If someone turns you down, that’s okay! 99% of the time it has nothing to do with you and its freeing you up to receive something actually meant for you! One of my favorite sayings: You can’t fuck up something that’s meant for you!

Listen To Yourself

How do you feel about yourself when you are with them? Do you feel like you can be yourself around this person? Be aware of what your body is telling you. Are your arms crossed or is your body language open and connected? What is your eye contact like? If and when they touch you, how does that feel? Does it feel good or safe? Is there an energetic attraction there? Or is there a friend vibe or no vibe at all? After you are done spending time with them, do you feel drained or energized? Do you feel relieved they are gone or can you not wait to see them again? Ask yourself these important questions!

Pick Someone Who Matches You

Date someone who compliments the person you already are! If you have to change who you are or your life to be with someone, that’s not your person. If you find yourself thinking “that person would be so great if…or they have so much potential” that’s also not your person! It is in no way fair to date someone who has a different lifestyle or different habits than you and expect or want them to change.

My dad told me a long time ago that you need to decide when you are dating someone, that if they never changed for the rest of their lives, would you be 100% okay with it? And be totally real with yourself on that. If you are a rose-colored/glaze over things because you are excited kind of person (me), go to your most honest friend and ask for a second opinion. (Thanks Megan! Lol) Date the person that fits into the life you are already leading. I’m at a really great place in my life right now, so I want to pick someone who is going to add too all the great things I’m already creating for myself!

And if you’re not happy with the life you are currently leading, maybe its not time to date yet, maybe its time to focus on getting to know and love yourself right now!

Take It One Date At A Time

In the beginning, try to keep things light! If it’s a good thing, you won’t have to rush it. Take your time getting to know each other and be yourself! You don’t have to decide if you want to spend the rest of your life together, take one day…or date at a time and have fun!

Published by Lorena Gregory

Kansas City local, writer, proud pet, plant and art owner, lover of things that matter, sunshine, music and books. I'm a curious, optimistic person who cares big and laughs loud.

2 thoughts on “6 Dating Tips for When You’re Getting Back Out There

  1. No kidding, thanks for writing this, old friend. I have literally zero experience with “adult” dating, and I find myself extremely intimidated by the prospect of it. Really just dreading it. Trying to be engaging to a woman I’ve never met before while constantly wondering if I’m doing something wrong sounds horrid. We’ll see how long I can put it off!


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