Life Advice



From 'it's a match' to first date: Steps for an easy transition from app to real-life

Erika Ettin, Tribune News Service on

Published in Dating Advice

After what can feel like endless swiping, seeing “It’s a Match!” pop up on your screen can feel like a victory. But let’s be honest: The journey has just begun.

There are still quite a few steps between achieving a mutual right swipe and meeting face-to-face. From sending an engaging opening message to setting up a first date spot, a lot can go wrong and have you back at square one — but here’s how to make the transition.

Start the conversation

You’ve matched with someone interesting — great! Now comes the all-important first message (or response to their opener). Look for message bait in the other’s profile, or anything that piqued your interest, whether they mentioned a hobby that you’re also into in their bio or posted a photo you’d like to know more about, and write about that with a question for them to reply to. Try something like: “That photo looks familiar — was it taken at the Music Hall? As a concert lover myself, I’m actually a regular there” or “It’s always nice to meet someone who knows their way around the kitchen. Try any new recipes lately… successful or otherwise?” Just remember that anything is better (and more likely to get a response) than “Hey” or “How’s it going?”

Don’t turn into pen pals

While it’s nice to have a flowing conversation, you are looking for a real-world connection, not someone to text with (I’ve often called texting “the death of the first date” or “the place where dates go to die” — and for good reason). If things seem to be going well, it’s time to suggest meeting face-to-face. I recommend making plans for the first date directly within the dating app. Once the date is scheduled, feel free to exchange numbers just for contingencies by saying, “In case you need to reach me tomorrow, my number is ___.” Your conversation-to-date conversion rate will be much higher.

Keep the momentum


Once you’ve got a chat started, don’t let it flounder. When things sit too long, they often just don’t happen. Here’s how to do it: “I'm enjoying our conversation. Would you be up for a drink this week, maybe Wednesday or Thursday after work?” Giving two days of choice makes it easier for the other person to say yes by giving valid options while still offering flexibility. Or, if you don’t want to ask so directly, simply say, “I’m enjoying our conversation. Where should we go from here?” That should lead to a date in no time.

Plan a casual activity

First dates don’t need to be rocket science. Keep it short and simple: meeting for a cocktail, chatting over coffee, or getting together for a walk in a public space are all great options. There’s no need for the added pressure of a fancy dinner or expensive tickets to an event with a relative stranger. It may be helpful to have a few restaurants, bars, coffee shops or parks in mind so you can make suggestions on where to meet.

Set realistic expectations

A first date is two people meeting each other — that’s really it. Go in with no agenda and no crazy expectations, keeping the conversation light about hobbies, upcoming travel plans, or things you enjoy. You are just seeing if you enjoy each other’s company. A great outcome is you leaving the date feeling good about yourself and the conversation.

Of course, this isn’t a foolproof plan. Someone might never respond to your opening message, they may ghost mid-conversation, or they might disappear from the app entirely as you’re making plans to meet. We never know what’s going on in someone else’s life, so all we can control is our side of things and keep the right attitude — easier said than done, I know, but still the truth.

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