A Toronto Matchmaker’s Advice: What To Do If You’re Re-Entering the Dating Scene Once Again

Toronto Matchmaker

As a Toronto Matchmaker we know that life happens and people change. And so, sometimes, you feel like it’s about time to get back into the dating scene (perhaps your long-term relationship just ended, for example) – but it’s been a while, so maybe you’re just a bit unsure about how to navigate the sometimes bewildering world of dating.

So here’s our little morale-booster for the just-splashing-back-into-the-dating-pool man: pieces of advice that’ll help make your transition into the dating arena a smoother, better, and more fun experience.

Dip your toe into this, and if you have any questions after perusing these dating pointers – getting in touch with our matchmakers is just a click away.


  • Elevate Your Fashion Look. This is another way of saying: become the most dapper-and-dashing man around. If you haven’t been in the dating scene for a while, it’s totally possible that you’ve let your fashion look slip a bit. So take the time to upgrade your wardrobe and elevate your look to something that not only neatly complements your physique but also reflects your personal taste, attitudes, and spirit. And – if you’ve taken an extended hiatus from the whole dating-part-of-life – it’s a completely smart idea to invest in an image or fashion consultant.


  • Activate Your Social Life. It’s often true: if you haven’t indulged in dating for quite some time, then your social skills – around women you could be romantically interested in – may need some polishing. That’s why it’s a great idea to become all-around more socially fluent and adept. You can achieve this by simply enlarging your social circle and your social activities – even something as simple as joining dance classes can make you incredibly more at ease in a wide variety of social situations you will encounter while dating.


  • Let’s Talk Hygiene. To be perfectly blunt, good hygiene can either make or break your prospects for a fulfilling dating experience. Dating requires a higher degree of all-around hygiene compared to other social areas of life (think about it – forgetting to brush your teeth probably won’t be as problematic when you’re on the golf course with a business contact than when you’re on that first hot date). So: good hygiene? Important! And it’s equally important to maintain this good hygiene throughout the dating experience.


  • Master the “Art of Getting Rejected.” Rejection in the dating scene can be much different than rejection in the business world. The former can sometimes feel intensely personal; the latter is – well, it’s business, and not personal. And if you’re not used to dating, getting rejected can be a disheartening and self-esteem-shaking experience. Anxious about rejection? Then master your emotions until you can get rejected every now and then without flinching – without taking it too seriously! Dating can be exciting, fun, thrilling, and a beautiful adventure if you can learn to let go and see where it all takes you.

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