5 Fun Ways To Ask Him Out

Can a woman really ask a guy out??

It’s a common worry. Most women see the idea as ‘anti-feminine’, or just too risky and fraught with potential embarrassment if it goes wrong.

couple on a date

Plus, we all know that many guys like to feel that they’ve been brave enough to make the move, and don’t want the woman to make things too easy.

But does that mean you should never ask a man out? Of course not. It’s not about whether you ask him out, it’s all about how you do it.

So in this article, I’ll show you 5 super-practical, easy ways to ask him out and still be a high value woman in his eyes:

1. Send him a pic with the message, “This looks awesome! I’m gonna check it out on Saturday. You in??” 

man texting

This is a great way to ask him out, because subconsciously you are telling him, “I want to go and see this anyway, but it would be fun if you joined me”.

It’s also useful because it gets him wondering, “Does she like me? Or does she just see me as a friend?” (That’s a good thing).

If he says yes to coming along, it means he wants to get to know you better and spend time alone with you, which is definitely a good sign!

It doesn’t mean of course that he definitely likes you romantically, as he may currently only see you as a friend.

So watch for his behavior on the date: him touching your hand, being protective of you, looking into your eyes – these are all signs he sees it as a real date. 

2. Bring him in with your group

group of friends having fun

 If you’re really scratching your head about how to ask him out, make it super-easy by just inviting him to a group event.

Now of course, ideally this could be a mutual crowd of friends where he knows some people too, otherwise it’ll get pretty intimidating for him to hang out with tons of people he’s never met!

In fact, this is an ideal way to ask out a guy from work and keep it really low pressure.

All you do is say to him, “We’re all going to go to that new wine bar that opened in town on Tuesday. You should come join us.”

If you feel the sparks fly between you on this date, you’ve then made it easy to take things further and put the ball in his court to offer another meeting.

3. Suggest something you know he already likes

croissants and juice

You’re both really into eating Sunday brunch and you found a great new spot? You both share a love of obscure superhero comics? You had a long conversation about your passion for wine tasting?

Text him with a link to an event or a cool place related to your shared interest and say, “I know you’d be up for this. Fancy checking it out?”

The beauty of this is that you are making the focus about going to see the place, instead of point blank asking him: DO YOU WANT TO GO OUT WITH ME?

Just make sure it’s something low-pressure, not something that requires expensive tickets and a huge day out. The easier it is, the better your chance to simply test the waters and see how it goes. Of course, if he’s up for spending the whole day with you that’s no bad thing either!

4. Go to learn something together

couple looking at art

 It’s always great to do a “date” that involves focusing on something that stimulates your intellect and curiosity.

Maybe there’s a speaker or a debate going on somewhere local that you can drop in on. Just ask him in person or by text, “I’m thinking of going to this at the weekend. Looks interesting. Want me to get you a ticket?”

[Pro tip: Make sure he’s into whatever you choose first! For example, don’t bother taking him to an art exhibition or a poetry reading if you think he’ll have zero interest in it.]

If you both have a good time, it’s the perfect opportunity to go for a walk and have a drink somewhere after to get to know one another more.

5. Do the bold move and just ASK!

couple having coffee

Ok, I said at the beginning of this piece that you generally want to use subtle ways to ask him out, but guess what?

Not every rule applies 100% of the time.

I once had a woman in the first conversation (after having approached me) casually say: “We should go for a drink this week.” It was bold, it was refreshing, and I was completely relieved when she said it.

But here’s the thing: You should only do this direct approach if you are going to do it with confidence and be relaxed.

If you’re in a high-pressure environment where you risk humiliation in front of others, or if it’s going to create tons of social awkwardness later when you see him in the elevator at work, then stick to one of the more low-key methods mentioned above.

Just remember though: the direct approach is always in your back pocket, and men love it when a woman occasionally takes the reigns in moving things forward (especially shy guys). So don’t be afraid to use it if you have to!

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There you have it: 5 simple but effective methods for showing you how to ask him out without any awkward conversations.

Play around with these examples and decide which one best suits the situation with the guy you’re speaking to.

Now all you need to remember is where you put that little black dress and those killer heels ;)

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12 Responses to 5 Fun Ways To Ask Him Out

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  1. Maria says:

    What if he procrastinates always, but never says no? I’ve asked him three times, and he always has something else to do and proposes another time, that sadly never arrives! Should I just give him up?

  2. Syd says:

    You narcissistic fucking asshole. You obnoxious prick! You are so full of yourself. Fuck uou

    • Syd says:

      hope you had fun sleeping with the girl from the gym

      You will meet many more

      Happy working out! I will enjoy mine

      • Syd says:

        I have been having an especially difficult time in MY life as of late. Everything I said is inconclusive

        • Syd says:

          and more emotionally fueled than factual

          • Syd says:

            Have a good weekend

          • Syd says:

            I’m tired & I was making myself upset. I wanted to vilify you. It was wrong to do that

          • Syd says:

            I must be a little crazy and this is not helping ease my doubt. I can’t lose myself.

          • Syd says:

            I’ve been through too much and I can’t engage in things that compromise my logic. It dents my confidence a little more each time

            I don’t have anyone in my life romantically. You’re a dating coach. I followed you for advice, developed a mild crush/obssession, and now Im leaving because I was spending too much time. It’s part of celebrity culture and happens to a lot of people. I can’t keep it to a limit because it may be delusion and unconfirmed doubts and it leads to suffering – I don’t want to suffer for a blurry cause

    • Lauren says:

      Hopefully your feeling better now, you seemed very troubled when writing this.

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