How to Turn Flirty Texting into a Real Date

Written by Imad Jbara | Edited by Hannah Madden

Last Updated: January 31, 2023 References

Getting the number of someone you like is a great accomplishment! If you aren’t sure how to turn that text convo into an actual date, you’re not alone. Fortunately, with a few tips and tricks, you can move your relationship forward in no time. Read through this article for advice on asking someone out via text to get an in-person date.

This article is based on an interview with our professional relationship coach, Imad Jbara. Check out the full interview here.

1

Show you’re interested with some flirty compliments.

Make your texting partner smile by telling them something you like. This is a great way to let the person you’re texting know you want to be more than friends.^{[1]
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Expert Source

Suzanna Mathews
Dating & Relationship Coach
Expert Interview. 18 August 2021.} Try to flirt with them via text every few messages so they know that’s what you want.^{[2]
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Expert Source

Mark Rosenfeld
Dating & Relationship Coach
Expert Interview. 11 June 2021.}
- You might say things like, “Your sense of humor is so good. You make me laugh every time.”
- Or, “That selfie you took is beautiful. I bet you look even better in person.”
- If the person you’re texting shows interest back, that’s great! They might give you a few compliments and respond quickly, which is how you’ll know they’re flirting with you over text.^{[3]
  X
  Expert Source
  
  Julianne Cantarella
  Dating & Relationship Coach
  Expert Interview. 6 August 2021.}

2

Try calling instead of texting.

If texting is getting boring, a phone call can be a nice way to switch things up. Hearing someone’s voice makes them more “real,” so the person you’re texting might start thinking about meeting up with you more than if you just stick to SMS messages.^{[4]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 22 September 2021.} Plus, if you’ve never met this person before, it’s a good idea to call them before meeting up in person, just to make sure they are who they say they are.
- You can suggest a phone call by saying something like, “Do you have time to chat on the phone tonight?” or, “Wanna FaceTime later?”

3

Start making in-person plans early.

Try not to text for weeks on end without moving things forward. Set a texting limit, like only texting with someone for a few hours (or days). Texting is fine, but texting someone for too long can often lead to the relationship fizzling out. Instead, make sure you try to set up an in-person date as soon as possible to move from texting to dating much faster.^{[5]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 5 November 2019.}
- There’s no set rules for how quick you should do this, but most people recommend texting for a few days at most before setting up a date.

4

Tell them you’re saving some topics for an in-person date.

If you chat too much beforehand, you may not have much to say on a date. Reserve some of the “get to know you” questions for when you meet up in real life. Otherwise, you could get to the date and realize that you’ve talked about everything there is to talk about—and that can lead to some awkward silences.^{[6]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 5 November 2019.}
- In general, it’s fine to ask someone via text what they do for work or what they get up to on the weekends. However, you should save the deeper stuff, like questions about their family or what their long-term goals are, for a real conversation.

5

Take some time between responses.

Texting back right away can make you seem too available. If you’re out and about and you’re busy, don’t feel pressured to reply to the person you’re texting. This will signal that you’re a busy person, and it will let them know that you’re probably not down to text 24/7.^{[7]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 22 September 2021.}
- Make an effort to match their response times, too. If they take an hour to reply, it’s okay to wait 45 minutes or so before responding.

6

Ask them what their plans are this weekend.

This is a subtle way to get them thinking about a date with you. If you want to start out slow, simply ask them what they’re up to this weekend or if they’re doing anything fun next week. If they aren’t, you can segue into asking them about their free time and when the two of you should meet up. Try something like:^{[8]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 25 May 2021.}
- “So, any fun plans for this long weekend?”
- “I’m hanging with friends on Saturday, but I’m totally free on Sunday. What about you?”

7

Suggest a fun activity to do.

A specific activity might seem more appealing than vague plans. Sometimes, people get nervous about meeting up in person because they’re worried about not having enough to talk about. You can suggest a casual activity, like mini golfing, bowling, or taking a walk in the park to put them at ease and get them to meet up.^{[9]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- You might say something like, “I heard there’s a new mini golf course downtown. Want to try that out?”
- Or, “I was thinking of going to that new hiking trail if you want to tag along.”

8

Suggest a specific time and place to meet up.

Hopefully, this can get your texting partner to commit to plans. Instead of saying “We should hang soon!” or, “Let’s get together sometime!” try throwing out a time, date, and place that you want to meet up. If that doesn’t work for them, they can suggest a different time and place so you two can actually meet up.^{[10]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 5 November 2019.}
- For instance, you might say, “Are you busy Wednesday after work? I could meet you at the bar near your house. Maybe around 7?”
- Or, “Let’s go to that new café in the morning! Does 9 AM work for you?”

9

Invite them to meet up if you’re already out.

This is another casual way to meet up in real life. Keep in mind that not everyone likes spontaneous plans, but if the person you’re texting does, it can be a fun way to meet up with them IRL. Invite them to the bar where you and your friends are, or have them meet you for coffee near your house.^{[11]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 28 September 2021.}
- You can suggest it by saying something like, “I’m out at a bar downtown, and my friends are about to go home. Want to join me for one more drink?”
- Or, “In the mood for some coffee? I’m at the cafe near my house getting some work done, but I could use a distraction.”

10

Don’t feel obligated to respond to sexual messages.

Unfortunately, sexting probably won’t land you an IRL date. You can absolutely sext the person if you just want a sexual relationship with them, but more often than not, it won’t lead to serious dating or a relationship. If the messages start to go that way or you’re getting a more seductive vibe, set some boundaries and let them know that you aren’t ready for that right now.^{[12]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 28 September 2021.}
- Say something like, “I’d rather we meet up in person before sending more explicit messages like that. It’s just a boundary that I’ve set for myself, I hope you understand.”

11

Move on if they don’t seem interested in meeting up.

Some people just want to stick to texting, and that’s okay. If you’ve suggested a few times and places to meet and they’re dragging their feet, they might just not want to go on an actual date. Chalk it up to a good learning experience, then move onto someone who’s fully interested and invested in you—you deserve it.^{[13]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 25 May 2021.}
- Some people find it helpful to set a texting timeline to know when they should move on. For instance, yours might be texting someone for 1 week before either meeting up or deleting their number.
- Remember that when someone’s not interested in you, it’s usually not your fault. It has more to do with them than it does with you, so don’t take it personally.^{[14]
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  Expert Source
  
  Judith Gottesman, MSW
  Matchmaker & Dating Coach
  Expert Interview. 19 October 2021.}