Archive:

Common Challenges of Dating in Your 20s and How to Overcome Them

Navigating the Maze of Dating in Your 20s Dating in your 20s can feel like a never-ending maze – full of twists, turns, and dead ends. Whether you’re trying to figure out what you want, dealing with rejection, or struggling to balance dating with other priorities, it can be tough to find your way. But […]

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Mix and Mingle: Tips for Socialising and Networking at Singles Events

Hello, all you lovely singles out there! Welcome to Cityswoon, where we bring people together to make sparks fly. If you’re ready to dive into the exciting world of singles events, mixers, and parties, you’ve come to the right place. Searching for “single events near me” can be a challenge, so we’re here to help […]

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Dating Etiquette 101. 8 Easy Tips Just for You.

It’s summer in the Northern Hemisphere – finally! Time to refresh on some simple dating etiquette so that you can make the best impression on a date, land a 2nd date or perhaps even a relationship or summer fling. Look Presentable With virtual meetings, being out of the office, and no in-person plans, we may […]

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Icebreakers for 2022 Convos

Spring is in the air in the Northern Hemisphere so warmer weather is finally here. After a long and challenging winter, people want to get out again and socialize. There will be birthday & housewarming parties, nights out at the bar, art gallery openings and so much more. No doubt people will want to catch […]

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Dating Rules for 2022

It’s a new year and it’s time to put your best foot forward. Make the most of 2022 by staying focused, thinking about how you can improve your dating life this year, and getting out of your comfort zone. With Valentine’s Day quickly approaching, it’s a good season to hone in and freshen up on […]

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Building Your Inner Confidence: 101

There is something inherently attractive about a person who exudes confidence on a first date. A confident person shines, from the way they carry themselves, engage in conversation, and care for others—it shows. Being a confident person helps in many areas of your life, both professionally and personally. When you are in the dating scene, […]

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The Dos and Don’ts of Dating After Divorce.

Dating, in general, can be an emotional roller coaster, but dating after a major life event like a divorce requires navigating many emotions all at once—excitement, fear, insecurity, stress, uncertainty. But taking a leap to date again can be a critical part of the healing process, allowing you to experience romance and love again. It […]

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5 Things to Keep in Mind When Selecting Your Profile Pic

By Saskia Nelson of Hey Saturday How you present yourself to the world matters. How you present yourself on your dating app profile matters even more. And it’s amazing how a handful of poorly chosen pixels could, potentially, derail your love life and, hold up your happily ever after. Here, though, are 5 things you […]

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5-Signs They Want a Relationship

By a Top Chicago Dating Coach You’re ready to meet that special someone to share your life (and you don’t care how long it takes). You’re looking for a best friend and a life partner. You want to make memories and have fun together. You want to be spontaneous and plan trips. You want to […]

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How to Avoid Awkward Date Questions and How to Respond if Asked Them.

The Third Degree Will Not Get You the Second Date While I don’t usually have calls with clients on the weekends (though, I still do work… dating never sleeps), when a client frantically texted me tonight to talk about a date (I’m writing this on a Sunday evening), I knew it was a call I […]

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