9 Matchmakers Share Their Best Dating Advice For Singles

To celebrate one of the many ways we find love, Aug. 31 is National Matchmaking Day. And while the practice of matchmaking goes way back (and may even give you flashbacks to your middle school chorus' rendition of the Fiddler on the Roof song) — we're certainly still seeing matchmaking reinvent itself in today's dating scene. From Patti Stanger's Millionaire's Club to services that match you up with other passengers on the subway to dating apps like Spritzr, which allow you to refer potential love interests to your single friends via Facebook, you could say that matchmaking is all around us.

So in honor of the professionals who pair us up when we're too busy to date, not finding quality matches, or choosing the wrong people again (and again), let's celebrate the holiday with matchmakers' best dating advice. After all, they've seriously seen it all with their clients. From not being afraid to go on a couple of bad dates to talking about your exes on a first date (yes, it can be a good thing!), here's the best advice the pros who save us from swiping on mirror selfie after mirror selfie have to offer singles about how to date better:

1. Don't Be Afraid To Fail

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"Expect to fail to succeed. Think of some of the current greatest innovators (Bill Gates, Steve Jobs, Mark Zuckerberg) and realize that they had to fail to succeed as well. Going on bad dates means you are THAT much closer to finding someone. If you don't try, you can't find love!" — Stefanie Safran, matchmaker at Stef and the City

2. Talk About Your Exes

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"Contrary to common dating advice — talking about exes on a first date is actually a great way to learn about the other person and quickly see if there are any red flags that they are not relationship material. While going into too much detail and rehashing the past can ruin the romantic mood, asking a few light questions about past relationships can be very revealing. For example, 'Are you still in touch with your ex?' or 'When did your last relationship end?' What you're looking for is that they speak respectfully about their ex, and don't immediately start venting about what that person did wrong. Bonus points if they have managed to stay friends, or at least that it ended on good terms. This shows real maturity, which is what you want in a partner. You'll also get a sense if there are still unresolved issues that might effect you if you get involved with this person." — Charlee Brotherton, relationship/dating expert and founder of Executive Matchmakers

3. Don't Rely On An Instant Connection

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"Sometimes looking for initial 'chemistry' can be an extremely limiting factor. Half the time That initial pull is indicative of lust, not even love, so if you are intrigued after a first date, give it a fair shot to see if chemistry grows with getting to know each other." — Erika Kaplan, matchmaker for Three Day Rule

4. Be Alert

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"Put down the smartphone — your person could be standing right in front of you, but your phone is shielding your eyes from him or her. We are all guilty of living in our phones, but that screen in front of our faces might be preventing the eligible [men or women of] the City from garnering the courage to talk to you and see where it goes." — Brooke Wise of Wise Matchmaking

5. Be The Best You Can Be

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"The best piece of advice I have for singles on this day is to be the type of person you want to attract. By that, I mean to be the best you can be so you attract the best. Too many people are tying to fill voids in themselves by looking for a partner who has the quality they lack. This may work on a surface level but it doesn't work on a deeper level." — Karenna Alexander, dating coach and matchmaker

6. Date Outside Your "Type"

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"Give people chances and date outside of your comfort zone. Date people you normally wouldn't date, especially if that same type isn't working out for you. Your type may have changed and you don't even know it yet." — Laura Bilotta, matchmaker and founder of Single in the City

7. Move Past Your Past

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“Everyone is hung up on someone, whether it’s real or in their head. You need to move past your ex boyfriend or that woman you went out with that never called you back. We have a tendency to compare people we meet to the ex files, and in order to find someone great, you need to quit this self sabotaging behavior. You placed this person who did you wrong, or never gave you a chance on a pedestal and they don’t deserve to be there. You based 'your list' on these people that didn’t work out, so toss your list!" — Susan Trombetti, matchmaker and CEO of exclusive matchmaking

8. Date Multiple People At Once

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"My #1 best piece of advice for singles is to date like you are The Bachelor or The Bachelorette! When you are in the early stages of dating, it's really helpful to date a few different potential future partners at a time (before you define the relationship with one of them, of course!). The beauty of dating multiple people before exclusivity is that you are able to date in a more objective manner without putting all of your eggs in one basket and becoming emotionally attached to Mr. Wrong.  You will be able to more clearly pinpoint the positive and negative qualities about your suitors, and allow your heart and mind guide who you think can give you what you desire in a more serious relationship." — Alessandra Conti, matchmaker and dating expert, co-founder of Matchmakers in the City

9. Always Be Ready

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"You never know who you are going to run into: whether its at a work or dentist appointment, the car wash on Sunday or running errands, if you're single you never know. So always take a minute to put some effort into looking your best. Looking your best adds to your sense of confidence and self-esteem and that resonates with everyone around you and draws the [potential partners] in like a magnet!" — Amber Kelleher-Andrews, relationship expert, matchmaker, and CEO of Kelleher International Matchmaking Services

Images: Fotolia; Giphy

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