Dating Coach Says to Avoid THIS Conversation Killer on Tinder

Jackie Rapetti
Hello, Love
Published in
3 min readApr 28, 2020

Online dating doesn’t have to be hard. It can even be FUN when you know what NOT to say.

Take it from dating coach and founder of Good Gentleman, Ruby Le. She knows a thing or two about what women want and what exactly men can do to charm their socks off. Online dating during the best of times can be isolating, exhausting, and frustrating… social distancing has magnified these feelings.

But just because you may be feeling lonely doesn’t mean you should mass blast your matches with ‘hey’s just to see who bites first.

Ruby’s advice?

“You need to STOP asking your matches, ‘how’s your day going?’ or ‘what are you up to?’ because –let’s be honest–we’re all rather limited in activities these days.”

Rather, Ruby suggests a bit more creativity when getting to know a match. The key is to make sure you’re learning more about the person instead of how their day was. “Try asking your match, ‘what was the highlight of your day?” or ‘what’s something you did for yourself today?,’” Ruby said.

By specifically asking a match to identify a highlight of their day, it will give you more insight into things that really matter to them. Plus, it’ll force them to consider a more meaningful answer than, “oh nothing much, what are you doing?”

In this current dating environment, all we have is communication. We can really focus on building an emotional connection versus all physical. Ruby says now is the time to work on your communication skills.

How well are you listening? How well are you validating, following up, and talking about yourself? It’s time to get comfortable with awkward silences and sharpen your ability to verbally compliment your matches; you can’t just give a kiss or hold someone’s hand to show affection right now.

Consider your values, lifestyle, and beliefs. While it may be great that you and your match both used to be in a band, love hiking, and enjoy concerts, those topics may only take a conversation so far.

So, your Tinder match likes to travel? Rather than asking them generic questions about their trip to Thailand, try digging a bit deeper. “Sometimes the easiest topics to start with lead to dead ends because you realized you learned more about Thailand than you did the person and it got boring,” said Ruby. What inspires them to travel and what have they learned from their travels are questions that may inspire more thoughtful answers about the person rather than the place.

And please do NOT ask your dating app matches how they’re holding up during quarantine in your first message. It’s become the new, ‘hey, how’s it going?’ and it’s not a great way to kick off a conversation.

Be creative, have fun, and be sure to follow Ruby for more dating advice here: @rubyloveadvice.

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Jackie Rapetti
Hello, Love

Native New Yorker. Cookie monster. Wannabe funny gal.