When Should I Message Her Again?

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Question from a Reader:

I’d been talking to a girl online, and after getting her number, I messaged her to schedule a date, which she was eager to do but couldn’t because of schedule constraints. When would it be appropriate to message back, or should she be messaging first this time, to try to schedule something again?


This is a great question and very common situation. I briefly discuss it in the third last paragraph of “The Ultimate Guide to Dating Apps Pt. 3“, but let’s expand on it.

From the sounds of the reader, he has had a few chats with the girl and she is interested in meeting up. That’s great, and it just means that you need to find the right time. The important thing to remember here is that she likes you and is comfortable enough to go on a date with you. With that in mind, you don’t have to do anything crazy or impressive, you just need to continue with this level of comfort until you find a day that works for you both.

I will break down the rest of my answer into two main considerations: who should message first, and how to get the date set in stone.

Should you message again first?

With regards to whether or not you should be messaging her back, it tends to vary depending on the girl. However, I have noticed a lot of girls will basically never message first or start a conversation via text until after you meet in person. Does this mean they don’t like you or don’t want to talk to you? No. It may be they either “aren’t the type to message first” (for some dumb reason), or they’re just not good at it/get enough attention from others on the app that they don’t really need to.

My rule is this: if the girl seems genuinely interested in going on a date with me but we can’t set up a date immediately, message her every 1-3 days to strike up a conversation and/or try and set the date in stone.

The reason for this is that you want to maintain the level of interest/comfort she has with you. If in this scenario you just didn’t message her for 5+ days, she may forget about you or why she was so interested in seeing you. If you are chatting every day or every other day, you stay fresh in her mind and when a day opens up where you are both free, she will be more likely to make plans with you.

Bottom line: you don’t have to message her every day (you can if your conversations are good and/or she has started a few conversations with you, showing she’s very interested), but make sure to be talking every 1-3 days to keep things fresh.

Setting the date down in stone

This is important, because you don’t want to get stuck in that “we’re talking but never gonna do more than that” phase. Therefore, you want to check in on your schedules every couple days to see if it’s possible to set up a date. Let’s go over one common scenario and how you can adapt based on how busy you both are:

Scenario: you guys hit it off online/over text at the beginning of the week (Sunday/Monday/Tuesday), but she says she has a really busy week but would love to go on a date when things clear up.

Your move: keep chatting her up every 1-3 days as mentioned, and on the Thursday or Friday during one of your conversations, ask her what her weekend is looking like. If she has some free time, ask if she’d like to meet you for a drink or coffee (read why you should suggest these here) at a certain date/time.

For example:

“Any big plans for the weekend?”

“It’s been a crazy week so I’ll probably hang in Friday but have a family dinner on Saturday, you?”

“I’m doing X, Y and Z, but I’m free Sunday afternoon if you wanted to grab a coffee”

If it works, great. If it doesn’t, you continue chatting every 1-3 days and checking in with that similar suggestion in a few days time. For example, maybe she can’t do Sunday but suggests the upcoming Tuesday. Or maybe she can’t do Sunday but says the end of the week next week works well. All you have to do is continue with the pattern: message her every 1-3 days to keep the chatting going, and a few days before the end of next week, ask her what her schedule is looking like and if she’d like to meet up.

This strategy can be adapted to pretty much any situation. For example, if you hit it off at the end of the week but she is going out of town for the weekend, just keep in touch and ask her what her availability is when she gets home. Rinse and repeat.

Lastly, and I mention this in a lot of my posts, but be patient and polite. Sometimes it may take time, although if they are clearly dodging or are making it hard to even keep a conversation going, it’s probably not worth your time.

I hope this clears things up, but feel free to leave your opinion, any questions or other comments you may have.

Thanks for reading!

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