CitySwoon Blog

Face to Face. Real People. Real life.

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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Valentine’s Day Outfit Ideas for Women

By Jen Zuckerman / @StyleintheFly Whether you’re planning a date night with your significant other, relaxing with your galentines or simply laying low on the couch to watch a romance flick, get inspired by some of these festive Valentine’s Day outfit ideas. I know that this night can come with some pressure to look a […]

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6 Ways to Prepare for Dating This Summer

By Benjamin Goodman After a long winter, the weather is heating up, restrictions are being lifted & relaxed, new venues are opening up & old favorites are reopening, plus many people have been vaccinated. All of this will lead to the return of in-person dating this summer as people are looking to resume their lives […]

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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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Do’s and Don’ts of Selecting Your Dating Profile Picture(s)

By Ali of @FindingMrHeight They say you shouldn’t judge a book by its cover. But on a dating app, the cover is all you have! Your first photo is what will make someone decide whether or not to read further. And often, it’s all they’ll see since so many people swipe first and only read […]

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