Should I Text Him? When To Hit Send & When To Wait

It’s the question we all ask ourselves when we start dating someone new: “Should I text him?”

You had a great first date last night. You haven’t heard from him since. Should you assume he’s following the three-day rule and will initiate contact soon? Or should you send him a quick text to reassure him that you had a wonderful time?

Here are some guidelines to help you determine when you should text him — and when you should wait.

When to text him: After a date

Rules are meant to be broken, right? There’s no reason to wait days to tell him you had a great time. Send a quick thank you, a throwback to an inside joke, or a follow-up to an earlier conversation. Keep it short and sweet. Your text will let him know that you’re interested. And then leave the proverbial ball in his court.

When to wait: The date ended, like, 5 minutes ago

Unless there’s a reason to send a text immediately — you still have his jacket over your shoulders and you want to return it before he drives off, for example — give your date a little breathing room before you send him a quick text. He might initiate contact in the next hour or so. Let him process the date a bit. He might be working up the nerve to send you a flirty message. Or he might be feeling a little insecure about how the date went. (If you feel he needs reassurance, text him that you had a great time so he won’t be nervous about asking you out for a second date.) But if you know the date went well, don’t rush it.

When to text him: He initiated last time

If he’s reached out via text, you should feel free to do the same. In fact, not initiating might make him doubt your interest in him. When it comes to initiating text conversations, aim for a balance of 50/50 so neither of you feels like you’re doing all the heavy lifting in your new relationship. Your initiation will affirm that you’re thinking about him, and want to take the time to let him know it.

When to wait: He hasn’t responded to your last text (or three)

He might be overwhelmed by your texting frequency. He might not be interested. Or he might just be too busy to respond right now. (Trust us, he hasn’t forgotten about you.) If he’s not responding to your texts, back off. Wait for him to initiate next.

When to text him: He’s reciprocating

If he answers your texts — and not just with one-word answers — keep engaging with him. Keep your texts short and infrequent. Don’t overwhelm him with personal questions or your life story. And make sure you actually have something to say. You can only text “hey”  or “what’s up?” so many times. If you watched that movie he recommended, let him know. And if something weird happens at work that you think he’d find hilarious, send him a quick message or photo.

When to wait: You’re not sure if you’re sounding needy

If you’re not confident that your texts are being well-received, ask yourself if you’re sounding (or being) needy. Still not sure if you should text him? Get a trusted friend’s input. Don’t text as a way of clinging to a crush. It will only drive him away.

When to text him: You need to.

Don’t play the “should I text him?” game with yourself if you really need to communicate with him. If you don’t remember where you promised to meet him tomorrow, text him. If you need to apologize (again) for spilling wine on his new jacket, text him. If you just came down with a serious case of something super-contagious, you should probably warn him to look out for symptoms.

When to wait: You need to vent

Having a bad day? If you’ve only been on one or two dates with your crush, it’s probably best to keep the life complaints to a minimum at this point. Anger and frustration rarely translate well over text. Try to reserve your typed communication for upbeat messages, not paragraph-long rants against your boss.

When to text him: You feel like it.

Sometimes it’s best to not overthink it. Be yourself. If you feel like texting him, do it. Be yourself. If he’s not into your texting style, maybe you’re not such a great match after all.