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How to Show Up and Crush a First Date (After Divorce).

Updated: Jul 28, 2023


If you’ve been out of the dating scene for a while - for some of us it may be 20+ years, it can be hard to imagine putting your self out there again. Dating can feel different than having a conversation with friends or co-workers (of course it is, you’re looking for a love connection!) and definitely different than the conversations you had as your marriage or primary relationship was coming to an end. So here are some tips to build your confidence back up and to remind yourself that you’ve got this.


1. Be curious. What are the things YOU are interested in learning about on this date? What information do you want to come away with after it ends? Think of things that are important to you and that will give you some insight into the values of the person that you’re meeting. Thinking about these questions in advance will allow you to feel prepared and give you some direction for the meeting. Of course, if the conversation meanders and gets legs, all the better - we ideally want there to be a natural flow, but having a couple of talking points in your mind before you start will give you a place to go if the conversation does stall. Begin with the end in mind! Set yourself a goal of 3 things you would like to learn about this person by the end of the conversation. This also gives you the opportunity to consider YOUR answers to the questions. This is not an interview, but it’s not NOT an interview. Your time is valuable and you should feel that you are making good use of it when being out on this date. Be curious. Aim to learn. Information is power and you are in the information-gathering phase.


2. Practice. If even the thought of meeting a stranger and striking up a meaningful conversation feels intimidating, then start small. There is no need to do “throw away” dates to get comfortable (but you can!). What we’re aiming for is for you to feel comfortable talking to anyone, because anyone could be your potential love match - you might just not know it! So practice. Start having random conversations with people you are in line with at the coffee shop, that you are next to when picking produce, ask an open-ended question to the person who rings you through at the grocery store. Get comfortable making conversation with new people. It could be as simple as asking how their weekend is going, if they know how to tell if a pineapple is ripe, or what kind of dog they have if you pass them on the sidewalk. Look for opportunities to engage with people - it doesn’t have to be anyone you would even date. It’s rather about flexing your conversational skills and learning how to connect with people that you don’t know.


3. Remind yourself when and how you feel your best. Is it when you wear that fabulous blue shirt, when you get up early and start your day with a good workout, when you allow yourself time to meditate or do something grounding. What are the things that boost your confidence so that when you walk into a room (any room) you feel like you can put your best foot forward? Carve out time to do one thing that makes you feel good every day. This is creating new habits. If you were in a failing relationship for a while, it might be tough to remember the things that made you feel good. As you begin your dating journey again, you have the opportunity to show up in any way you like. There are no preconceived ideas of who you are, so why not take the opportunity to be the person you dream you can be. Make sure to incorporate a few of those things into every day and especially on the day that you’re prepping for your first date. It’s not about making an impression on the other person, but rather equipping yourself to feel your best.


4. Fake it til you make it. Who do you dream to be? How do you want to show up this time around? Are you the witty person who engages through smart humour, the person with enviable edgy style, the person who has passion for life and isn’t afraid to show it? How do you want to shine on this date? Perhaps you go back to a time when you WERE that person - remember how you felt, how you interacted, the lightness you carried when you could show up authentically and without guard? In this great quote from Hades, we are reminded that “It’s never too late to create the you, you want to be”. Use this fantastic opportunity to do just that.

There’s no arguing that the emotions you may feel as you head out for your first date could be as varied as the outfits you try on! Butterflies, nervousness, fear and excitement all remind you that you’re doing this; you’re engaging again - a win! Give yourself a high-five and make the most of it. By using curiosity, creating connection, putting your best foot forward and being authentically you, you may just surprise yourself at how good you are at crushing this (next chapter) first date!




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