How To Go From Chatting Online To Dating In Real Life

Alexa Weeks

Oct 26 2023

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If you’re looking for someone to meet for a quick hook-up, that’s easy. Go on Tinder, swipe right, and have a quick fling within a few hours. But if you’re looking for someone with whom you can spark a connection and grow a real relationship, then you will need to slow down.

The transition between chatting through online dating and dating in real life comes much easier when you have something to build on with that other person. Choose to talk to people who truly interest you rather than people who you think are a safe bet. Take your time getting to know them in the beginning, that’s the fun part anyway! Need some ideas for conversation starters? Check out this article to learn some great openings to online conversations. The part where it gets a bit tricky is deciding how and when to make that jump of meeting in-person.

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It’s true that navigating this whole transition process can be intimidating and overwhelming for all of us, but even more so, it can be exhilarating and fulfilling. The problem is, sometimes you just don’t know where to start! That’s where I come in. With a few expert tips and some keen dating insight, you’ll gain the confidence and skills to move from the single life to a life full of possibilities in love.

The tips you’ll read here today will help you understand and even plan this entire process, from getting to know them online to sitting across from them in person. Let’s get started!

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Tip 1 – The 5-day rule

Don’t even think about asking someone out before day five. That’s right, five days is the time it takes to build the bare minimum of the most crucial element to dating: trust.

Trust is built by getting to know someone, becoming familiar with their personality, communicating sincerely, and getting comfortable with your mutual interactions.

If you ask someone out on a date before they’ve built that level of trust, then they are more likely to decline or back out on your invitation altogether. You want the other person to be waiting on pins and needles for you to make the move, rather be taken aback by your seemingly senior actions. The best is to meet within the first two weeks of dating online – studies show that after about 14-17 days, people started to feel let down after this two-week tipping point.

Tip 2 – The chemistry test

Find out if you have that special chemistry online! This sounds pretty elementary, right? But think about it. Many people who join an online dating website get impatient and start asking out or accepting dates from anyone who comes along regardless of their genuine compatibility. Nine times out of ten, this leap of faith goes horribly wrong, spiraling down before you realize that there is no chemistry, and with no chemistry, there is no future. And now you are completely jaded and have decided to join a convent!

So, test out the waters. Play with that person through conversation. Feel them out. Do they banter how you like? How’s their sense of humor? Do they ask questions about you? Can they carry a conversation?

Tip 3 – Build a rapport

After a couple of days, when you’ve decided that this is the person you want to ask out on a date or who you want to ask you out on a date, start moving in closer. Send those ‘Good Morning’ texts to show that you’re thinking about them, ask how their day is going and share details about yours. What you’re doing here is painting a picture of what it would look like if this became the norm. Now, the infatuation starts to build.

Don’t be afraid to get old school and ask for their number. A phone date is a really great way to break the ice before a face-to-face date. Not to mention, it’s quite romantic in this day and age.

Tip 4 – Propose a date

Once you’ve passed that five-day mark, you and the other person must be itching to meet in person. Although you may feel nervous about that intimidating first date, you are excited about the person you will be dating.

Think back to your conversations and what you know about this person. Do they love sushi; are they vegetarian; do they like to unwind after work with some wine; did they say that they can kick your butt at bowling? By now, you have plenty to build on in order to come up with that perfect first date proposal.

Make your date suggestion casual:

 “I think it’s about time I challenge you to a round of bowling.”

 “I know you like pizza, I’d love to take you to my favorite pizza spot this weekend.”

“While I really like talking to you online,  I imagine talking to you in person would be even better. Are you free on Friday?”

If you’re still stumped on the perfect first date idea, check out this list of ten date ideas that don’t suck.

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Tip 5 – Make sure you’re comfortable

If someone you may be interested in going on a date with asks you out before you’re ready, don’t say ‘No’ immediately. They might be put off and never ask you again, and that will be the end of any potential relationship. Instead, stall them. If you need more time, tell them “This week is really busy for me, let’s try something next week.” This way, the other person is still hopeful and you both will take the time to continue talking. This also puts some positive pressure on you to take whatever steps to feel comfortable by that point and deciding if you’d like to meet.

Dating isn’t easy. In fact, online dating isn’t even very natural. While online dating provides the benefit of great algorithms to help find a match, we can’t read someone’s body language or feel the mutual chemistry between us and the stranger on the other side of the screen, so it can be pretty hard to analyze how well our interactions are going. What we can do is be sincere in getting to know someone while allowing them to get to know us. When the time is right, seize the moment no matter how scary it may be.

Trust me when I say that even the most attractive, most experienced, and the most confident of people still feel like asking a person out on a date online is uncharted territory. You are not alone! We all want the same thing: to love and to be loved.

Once you’ve locked down that first date, be sure to check out the First Date Survival Guide, so you’re prepared for every situation!

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