Kate Holmquest | April 17, 2015

3 Ways to Take Your Online Relationship Offline

Let’s get one thing straight. There’s no such thing as online dating. Until you’ve actually met the person face to face, you’re only dating an idea.


Dating a person you met online is what I like to call, simply, “dating” – but getting there can be frustrating.

Maybe it’s happened to you: you have amazing texting conversations with someone that actually make you laugh out loud. Finally, you go on a real date with them and all you hear are crickets.

Many single people scrap their dating sites and apps after a few of these frustrating encounters. After all, no one starts a match.com or tinder profile dreaming of endless flirty texts and email exchanges.

But there is a purpose to the online phase of a relationship that’s forming, and an art to successfully navigating the transition to being together offline.

Here are a few checkpoints to follow before and during the date:

1Chat on the phone before your first date

Before meeting them in person, try having a phone conversation first. It’s not about whether the person on the other end of the line has a sexy voice. It’s about how engaged they are with you, how curious, how well they read your moods and cues, and how they flow with you. If you’re bored after five minutes, or if they haven’t made a move by the end of the conversation to seal the first date, it’s not worth your time.

Follow your gut – it’s better to have a mere five minutes of awkwardness rather than waste a whole night with poor company.

If the conversation goes well- fantastic! You can expand on your conversation on the date, and your first meeting will be less awkward.

If you look back at any relationship that lasts, you’ll see how that first conversation planted the seed for so many conversations that followed, and how the challenges and delights you have at date 15 are many of the same ones you had in that first 15 minutes.

Don’t miss the chance to get some great data from the comfort of your phone before meeting in person. Without the additional pressure of having to think about how you look, how they look, what face you’re making, and the constant interruptions of a waiter, you’re in a better position to check in with yourself on what you like and don’t like about the conversation.

2. Keep your first date low-key

When you’re meeting your date for the first time, keep the date simple. Going to a concert or a trapeze lesson might be a thrill, but you’re better off picking a venue you’re sure you can have a conversation in.

The perfect solution is to set up a series of plans, right? Dinner and a movie is classic. Or coffee followed by that concert you want to see. Not so. If your date is going down the drain after ten minutes, you’ve just made it nearly impossible to exit gracefully, and you’re likely to have your dud of a date ruin an otherwise cool experience.

You’re better off keeping your cards to your chest, and if you’re loving the company, mention that cool thing going on nearby you’re planning to go to, and see if your date will join you impromptu.

3. Ask for feedback!

Towards the end of the date, be up-front and ask questions. Ask your date how they think the date went.

Better still, be the first to give feedback. For example, if your date’s not making eye contact, mention it at the 30-minute mark in a light way like, “Hey you over there, I can’t get a read on you because you’re not looking my way much. Are you having a good time?” Your date will show their interest by telling you what’s on their mind or meeting your eyes more for the rest of your time together—or they’ll be defensive or deflect your comment. Either way, it’s important to see how they engage with you when you’re truthful.

Don’t be that person that tells someone, “Let’s go out again!” then vents to her friends about their date’s every awkward move on the way home. Or that person who’s left wondering why she didn’t call. Hear it straight from your date so you can adjust how you are on dates, or adjust the kind of dates you choose.

If you’re the great catch you think you are, you don’t have time to waste online. Get just enough info to decide if a person is worth your time to meet, and get out there and engage offline!


About the Author

Kate Holmquest

Kate Holmquest is a coach, curriculum developer, and campus director for Wright and the Wright Graduate University for the Realization of Human Potential who believes that dating is one of the best possible playgrounds for discovering and transforming yourself! Potential movie titles that describe her quest for satisfaction in single life are “40 First Dates” (a.k.a. dating with velocity), “Ten Things I Hate About You” (a.k.a. telling the truth on dates), and “The Thing About My Folks” (a.k.a. noticing and breaking the relationship rules I learned at home). 


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Image courtesy Flickr user cgpgrey

Wright Living is a division of the Wright Foundation for the Realization of Human Potential, a leadership institute located in Chicago, Illinois. Wright Living performative learning programs are integrated into the curriculum at Wright Graduate University.

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