How Gentlemen Ask Women Out On Instagram

Making the first move is no less trepidatious online than it is offline. Will this be love at first like? There's only one way to find out with this etiquette guide on how gentlemen can ask women out on social media non-creepily.

Should you message her? Technology changes and our mediums change, but the indecision and wracking up of nerves to make any first move from a gentleman to a lady remain a barrier for many.

I cannot claim to have a humongous wealth of experience here - actually, thank heavens for that! However, I have some experience in this exact area, which may be helpful to some, not least from an etiquette and communication point of view too.

If you want the short answer in less than two minutes, feel free to skip right to the last point in the article. Although, you may benefit from the full read for some proper context as well as some useful insights to keep in mind.

Ask yourself if this woman is really who you want to ask out

Did you match them on Hinge, Bumble, Tinder? Doesn't matter. Everyone knows Instagram is the real dating app of the modern world. Instagram is the place to see more of who somebody really is.

You should look at their profile to gauge what they are like as a person to the extent that it is possible. Are they always complaining? Do they have ‘London/Dubai’ in their bio? How risqué are their holiday snaps? Live and let live, of course, but if there is something that doesn't align with your idea of the perfect partner - whatever it is - then maybe don't get your hopes up about it, if you decide to bother at all.

What is your first move?

You should take it upon yourself to make the first move. That’s what most women will expect. That's not to say you can't look out for any signals of interest. For example, that she has followed you back and viewed your story. Good start.

It's nothing new for women to offer the opportunity for men to make the first move. In the Victorian era, women would wave their fans or drop their handkerchiefs on purpose to catch the interest of a gentleman they'd like to notice them and so they could make the ‘first’ move. Nothing much has changed except the inability of modern men to pick up on these signals. Still, if she does not make any signal, it shouldn't stop you from using your initiative to slide right in there.

Testing the waters before making an actual move could save you some time. It's not necessary, but I would advise it anyway. For example, liking one recent photo (not necessarily the latest) and/or liking a story. You may think they won't pay any attention to this, but they will. Trust me. It might be reciprocated.

Keep the thirst to a minimum

Women can detect desperation. One photo like or one story like is enough. You only need to be in the frame, not right in their face, as that smacks of desperation.

I know reacting to the selfie story with the fire emoji feels like you can basically start planning the wedding, but in reality, it signals a half-hearted and maybe crass attempt that resembles a first move without the confidence to say anything that constitutes a proper first move in the eyes of a woman.

Strike while the iron is hot (don't wait weeks or months to message her)

If you don't make your move, someone else will. Gentlemen have initiative and don't let opportunities slip away. That woman you like is most definitely in the sights of other men too. This is a player-versus-player world. If you don't make your move, someone else will. The worst that can happen is she ignores you or says no, and that’s really not that bad, is it?

After whatever photo or story like, give it a couple of hours, a day, or a couple of days at the most.

What should I open with? What do I say in the first message?

I’ll disappoint you immediately by saying that there is no right answer. There is no panacean ‘line’ that works every time. Sometimes, the maturest of cheddar lines used ironically can work. Other times, a seemingly innocent serious thought in reaction to a story can spark a great conversation.

The main thing is that you say something as original as possible, honest, authentic, maybe complimentary, or something funny. Only you in your exact situation will feel intuitively what makes sense to say.

Even if your opening gambit was not well-received, it doesn’t end there.

Steering the conversation

There is an end to which all of this is directed. Once you’ve made your first move, it’s key to not let things float around in meaningless chat and empty back and forths. Using your gentlemanly qualities of humour, intelligence, and charm, you should always be subtly steering the conversation gently from topic to topic; allow for the words you both say to develop the conversation organically.

It’s not about getting her number

If your sole aim is to get a woman’s number then it’s more likely you will fail to establish a real rapport upon which any meaningful step forward can take place. The goal is to establish some kind of genuine connection and maintain it.

How to ask a woman out like a gentleman and non-creepily

Finally, we have arrived at the question we set out to answer. I have to say, there is no silver bullet that can strike the right cord and work its magic with everyone, all the time. Luck is a considerable part of success in anything, more than we like to give credit for. We want to try and break everything down into exact formulas and strategies that will replicate someone else’s success, but it sadly does not work like that.

Having said that, there is a way you can make an effort smoothly to ensure greater chances of success. Here is one way I would do and have done:

When the conversation is at its peak, and things are going great (10-20 positive messages have been exchanged (any fewer requires further building)), make a clear suggestion to meet up somewhere with some specific idea or theme of the meet-up.

Would you love to hear more about her big work project you were just discussing? Of course, you would. There’s one good reason. Maybe she is from another city and has never really been near your city centre, that’s another good reason. Whatever the idea, there just has to be one. Going out for the sake of going out might be tempting to some women, but it’s nicer to offer some context and purpose to meeting up beyond meeting up’s sake. It sounds friendlier, less desperate, more genuine, and thus more tempting to say yes to.

Should you prove successful and want to know how you build that chemistry on your first date further still, then I refer to a previous article I’ve written.