When Should You Ask an Online Crush If They’re Single?

Photo by Kirsten Drew on Unsplash

The world of online dating calls for new etiquette about when certain things are appropriate. When not using a dating app, where it’s usually assumed that both parties are single, a lot of questions about the “right time” to bring things up might arise.

Should you ask someone if they’re single right away or wait for a few exchanges of emails or messages? Should you tell them you’re single or is it better to ask them first? These are some of the questions people are trying to figure out now. This post will attempt to answer them.

Should You Ask If They’re Single Right Away?

Unless you’re using a dating app or in a singles-related discussion, you shouldn’t lead by telling someone you’re single. Don’t mention that in your first message to them.

Get to know them first. Exchange a few messages back and forth. See if this is someone you could actually see yourself in a relationship with. Get to know them as a whole person, not just a name and a picture on a screen.

If you lead by telling them you’re single, you’re also telling them right away that you’re desperate. As I mention in this post about why your love may often be unrequited, desperation is an unattractive quality. It basically tells this person, “I don’t really care who you are. I just want to be in a relationship with someone, and today I’m picking you.”

People like to feel special. They like to feel chosen for a reason. They don’t like to feel that you’re just picking them at random. If you lead with desperation, it doesn’t make them feel special. And it will often lead to rejection.

Exchanging a few messages back and forth will also allow you to tell whether this person is compatible with you. When you’re desperate, you don’t care about compatibility. You just want to have someone now for some reason—you feel lonely, you want to prove to yourself or others that you can have a relationship, you want to make an ex or a crush jealous, etc.

All these are less-than-ideal, if not superficial reasons to enter a relationship. If you want to have a solid relationship with someone, get to know them first, see if you’re compatible, and then ask if they’re available.

Should You Tell Them You’re Single First?

This is one you should try to feel out. It can go fine or come out awkward either way.

You can tell the person you’re single and then wait for them to reveal their relationship status, which they may or may not do. If they don’t, then you can ask. Or you can ask them first and then tell them you’re single if you find out they are, too. If they’re not, it’s up to you whether you still want to reveal your relationship status.

I will say, though, that if you tell them you’re single and then ask them if they are in the same message, it still comes out with a hint of desperation—though not nearly as much as if you lead with that detail.

Just think about how you would ask someone their relationship status in real life. Would you tell them you’re single first or would you ask them? Don’t make it seem like the world of online interactions is so completely different from real-life interactions.

Things like kindness, decency, authenticity, and common sense are important in the real world, so you should absolutely use them in your online interactions as well.

And you can always go with the subtle, but not-so-subtle tactic of assuming they have a partner and waiting for them to confirm or correct the assumption. For example, you can say something like, “I’m sure your partner is happy about that.” After they either correct you or confirm what you said, you can decide what to do next.

How Do You Know When to Tell Them?

Again, you have to feel this out. The precise “right time” will depend on a variety of factors, such as whether you sense this person enjoys talking to you, whether you want to get to know each other better, whether you feel any chemistry, or whether you sense you’re on the same page.

It takes time to feel these things out, so don’t rush the question. Wait until you sense that it will be welcome or until you realize you probably won’t ever be sure and feel the need to know.

Remember, you don’t want to fall in love with someone, only to find out later that they’re in a relationship. So, if you’re really interested in dating them, it’s important to get this information sooner rather than later. But, again, don’t rush it.

If They Say They’re Single, Does It Mean They’re Interested?

It’s important to keep in mind that some people reveal their single status, not because they’re interested in a relationship, but because they’re just sharing general facts about themselves. So, don’t assume that a revelation of this kind means the person is interested in you romantically.

If they tell you they’re single and you want to know whether they would like to date you, be on the lookout for the clues they’re likely to give.

If, for instance, they tell you they’re single and then don’t ask about your relationship status, they’re most likely just revealing general information. But just because they’re not interested in you romantically now doesn’t mean romance couldn’t blossom from your relationship. You just might need to be patient.

But they could also be shy about asking you, so pay attention to whether they try other, more subtle ways of finding out if you’re single.

Final Thoughts

I’ve never been the biggest fan of dating apps. But I’m very aware that since so much of our interactions these days are virtual, it’s becoming more and more common for people to find interesting and intriguing people online.

They may meet over a common interest or a hashtag that drew their attention and then start a conversation, eventually moving from the platform where they met to a more private one.

Throughout these interactions, questions about the right time to do things will frequently arise. This makes sense because online dating is still a relatively new phenomenon, especially when you consider for how much of human history it didn’t exist.

I hope the advice in this post helps. But if you have any other questions, feel free to leave them in the comments below.

Now I turn it to you. When do you think is the right time to ask an online crush if they’re single?

~ Ashley C.

Last updated: February 17, 2024