Cupid's Pulse Article: Ask The Guy’s Guy: How to Win a First Date After Meeting OnlineCupid's Pulse Article: Ask The Guy’s Guy: How to Win a First Date After Meeting Online

By Robert Manni

Question from Gillian L., Manhattan, “Hey Guy’s Guy, whats the best way of turning an online connection into a real date?

You have a match on your favorite dating app and the conversations online are taking off. You’re up for hours talking to your match but you’re nervous about meeting in person. How can you be sure to impress on a first date when you’ve already gotten to know each other? How do you make a successful transition from online to in person dating? Read dating advice from our relationship expert Robert Manni!

Score That First Date!


We live in a wired world so these days connecting with new people often begins online. As a result, in business and dating, we need to develop an authentic, online voice that others like and can relate to. We make our connections online with a goal of meeting in person to close the deal.

When it comes to dating, after making a new connection online, scoring an in-person meeting can be challenging. With all the texting and emails we send each day, online communications are second nature for us. As a result, some online daters become nervous when it comes to leaving their comfort zone behind the keyboard and actually meeting someone new in person. But, it must be done because no matter how much texting or how many Facebook or Instagram posts you share, romantic connections only happen when you meet face-to face.

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So, after you’ve made a potential online love connection how can you quickly and seamlessly move the process ahead? First, keep the online correspondence brief and always pointed towards the ultimate goal of meeting in person. What’s worked for me is after exchanging a few brief texts or emails with someone new, I send my number and suggest a phone call. As a guy, this validates that I am who I say I am and is sharing my real phone number. It’s a minor display of truth and vulnerability.

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If the woman is interested she would usually send her number. Then, I make the first call. The process may work a bit differently for women. If you are interested in a guy and he’s dragging his feet, if everything else feels right send him your number or ask for his. The goal remains the same; exchange numbers and have a phone call. Energy is exchanged when you hear a person’s voice for the first time and hold a conversation with them. A phone conversation is a qualifying step before you decide on meeting someone new.

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I suggest keeping the call brief. It’s easy to get excited and share too many personal details with someone new, but you also can waste a lot of time chatting on the phone with someone that you don’t feel the sparks for in person. Keep the call short and keep the process moving. If things feel right, before breaking off the call, casually suggest meeting up and continuing the conversation in person. Drinks, coffee, whatever feels right for a first “date”. If the guy shows any hesitation and does not jump at the chance to meet a woman as dynamic as you in person, move on.

Hope this helps. Good luck!

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