Dating Restart: How to make the most of modern dating after a breakup

Article Courtesy of Oona, Discreet Introduction Between Unattached Professionals

Putting yourself out there again after a major breakup is never an easy task. All of the pain and insecurity from your last relationship most likely hasn’t healed 100%, and you may be afraid of making the same mistakes twice.

To make it more complicated, modern dating is confusing, especially for those who haven’t been in the dating pool for a significant period of time. Texting, dating apps and hookup culture can make for a cesspool of manipulation and hurt if you don’t enter into with with intention, clarity and a rock solid sense of self worth.

To help you navigate the often murky waters of dating in the mobile age, I’ve summed up my experiences as a matchmaker and dating coach to help you, decide whether you’re ready to date, and if you are, to make it a fun, positive experience that catapults you to a greater sense of self-awareness and even deeper love.

Check Yourself

Before you sign up for that hot new dating site, I have one question for you: are you truly ready to have a relationship? Dating is one thing. Dating is fun. Dating is exploration. Dating is a journey. Relationships are a whole different bag, but as I’m sure you’re aware, dating often leads to a relationship.

If you go on one date and meet “the one,” can you honestly say you’re ready to begin the process of meshing your life with another human being so intimately? Have you taken the time to figure out who you are outside of a partnership? Have you taken the time to date yourself, and determine what your wants and needs are? Are you stable? Capable of supporting yourself physically? Emotionally? Spiritually? Financially? If you do meet that great person, are you on solid enough ground to not be consumed by it?

If your answers to these questions are “no” or “I have no clue,” then I’d recommend waiting to start your dating journey until you’re a bit further along. You can work with a therapist or coach, or read a myriad of fantastic books out there to work out the answers to those questions for yourself, that way when you meet that great person who has also done this work and has a solid sense of who they are, your relationship can be built on a solid foundation.

When I’m working one-on-one with clients, I make them go through an intense period of introspection to determine what it is they want and need out of their next partnership before embarking on an intense and focused dating period. During this time, they not only assess their needs, but answer the questions: what do they bring to the table and where do they need to grow in order to be the best partner they can be?

It’s so easy to reflect upon your last relationship and place the majority of the blame on your partner. To think that you don’t need to grow. The problems were all THEM. That type of self-righteous thinking is not a person who is ready to enter into their next relationship because even if your ex sucked more than a sour lemon drop, you still chose to remain with them for as long as you did. Having the ability to acknowledge personal responsibility without placing all of the blame on either yourself or your ex, is a sign that you’re ready to move on.


Know How You Show Up

Are your limiting beliefs keeping you from showing up fully and finding love?

It was a warm spring day in Barcelona, Spain. I was in my early 20s living as an au pair with a family in the heart of the city. That afternoon, I’d decided to skip my Spanish lessons and instead wander the 1000+ year old cobblestone streets instead.

The sun had been a recluse the past few months. Soaking in the warmth, my smile was infectious. No matter who I passed, someone would meet my eye, and smile broadly in return.

That simple day, was one of my happiest. Whenever I recall it, I can feel the sun on my skin, see the cobblestone streets, and see all of the smiles beaming back at me.

Danita Barcelona. That’s who I am. I am that moment — always. I am radiant joy. I am open. I am a constant smile. I just have to remember to bring her out. Share her with the world. When I do, the world comes to me, is pulled into my intense gravitational field. That’s when the best things happen in my life. New loves, new friends, new opportunities. They all get caught up in Danita Barcelona and have no choice, but to wrap themselves around me.

When I’m down someone other than Danita Barcelona comes out. And she does the opposite of Danita Barcelona. She repels loves, friends and opportunities from her. She’s not fun to be around and she misses out on the greatest joys of life…the connections we build with others.

Which one are you most of the time? If it’s not your version of Barcelona, I can only imagine the phenomenal experiences that are passing you by.


So now that you’re as ready as you can be, it’s time to do some exploring. Meeting someone of the opposite sex can be tricky as men and women tend to have very different interests. It helps to have clarity around the type of person you want to be with because you can try and get inside their mind. What would your ideal date like to do? Would they join a sports league? A cooking class? A painting class? Theater in the park?

Now is the time to try all kinds of new things that you wouldn’t have before. And don’t be afraid to go by yourself. You’re dating yourself remember?

Want to try indoor skydiving? Do it! Hot air balloon ride? There are tons of companies near by, so why not give it a whirl?! You never know who you’ll meet or what you new interest you’ll develop.

The key is to stay active and constantly meet new people aka expand your tribe. Dating is nothing more than a numbers game. The more people you meet, the more likely you’ll be to find someone that you click with. Even if you’re making new friends, you never know who may know the love of your life, so get exploring!


Have Fun & Temper Your Expectations

The hardest part of dating, especially when dating online, is getting your hopes up as to who this other person is, and what they could be to you. Having expectations that are too high is a one-way ticket to disappointment, so make sure you keep your expectations to a bare minimum. In fact the only expectations I recommend you have for each new prospect you meet are to a) have fun b) learn something about your date c) learn something about yourself.

That’s it. If your date isn’t fun, do your best to bring that energy. If we all spend our time waiting for someone else to show up authentically so that we can then feel safe enough to show up as our best selves, that’s a lot of time spent waiting, which is ultimately time wasted.

Oh! And let’s not confuse expectations with boundaries and respect. You can have low expectations and still expect your date to be kind and thoughtful. If your date is being rude, call them out on it, because they may not realize they’re offending you. If they continue the behavior, politely end the date and don’t look back. Remember, your time is your most precious resource. Don’t just give it away to anyone who doesn’t appreciate or deserve it.

Cut Through the B.S.

Games. Games. Games. I intensely dislike dating games and the people who play them. If you want a solid relationship not filled with games, then make sure you don’t play them. Throw the rulebook out the window and be authentic.

Don’t like texting? Politely say so while making your preference for phone calls or in person meetings clear.

If they invite you out last minute and you’re available. Go! Just make sure they don’t make a habit of it because that could be a sign of you being a convenience. Overall there’s nothing wrong with being spontaneous, in fact it’s exciting and sexy!

Did they message you and you’re available to respond? Then message back. Don’t wait three days. It doesn’t make you seem interesting and mysterious. It just makes you seem aloof, uninterested and rude.

Dating doesn’t have to be a miserable experience. In fact it can be fun and exciting, but you have to have the right mindset to show up and make it so.

Be honest with yourself, be honest and clear with your dates and there’s no reason that you can’t find the right one, in no time.

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