a couple of years ago

4 Things To Do When Asking Someone Out + 10 Cheap Date Ideas


Sadly, the art of courtship is dead. 

Instead of being charming and original when asking someone out, we opt for a quick text asking someone if they want to hang out. And unfortunately it works because sadly that's the state of dating right now. But it doesn't have to be. 

You. You're different, and you're ready to take your game to the next level. Use these 4 upgrades to dramatically increase your odds of going on more dates. ​


Look, I get it. We're all busy. So let's just jump right in!

​4 Things You Should Know When Asking Someone Out + [10 Cheap Date Ideas]

1. Be Specific About What You Want To Do

I’ve said it time and time again but it’s worth repeating: Women don’t want to hang out. They don’t. They want to do something fun, and hanging out is just too vague to get excited about.

When I’m looking forward to a date, its because I’m excited to spend time with someone, and interact with them in the context of the activity we’ve chosen to do. 

I went on a date last month and we ended up at a musical performance for a student’s Master Thesis. It was weird as fuck, totally random, and really fun.

Asking someone to hang out is vague, and it’s cowardly. Here’s a video for you about it.

Need some ideas? Here’s 10 right off the top of my mind:

Ten Fun Cheap Interesting First Dates

  1. Ferry ride across a body of water, and back!
  2. Bike ride to a new park, drink tea in the park.
  3. ​Go to a museum when kids aren't allowed (the adult swim version of museums).
  4. ​Go to a yoga class together and check out each others butts.
  5. ​Go to SPCA, pet all the puppies and kittens (allergies permitting).
  6. ​Open local newspaper, go to a random $5 show.
  7. ​Go watch cringe worthy open mic comedy (see you there!).
  8. ​Set up a lemonade stand and sell lemonade for 5 cents.
  9. ​Go find a swimming hole. Bring bathing suits. Hope you don't have to wear them. 
  10. Go to a park, find a slackline and ask people if you can practice.

2. Find Out Something About Them Before Asking Them Out

Be curious about the person you’re talking to. If you ask someone out without having developed any rapport or knowing anything about them, it’s clear that you’re only interested in their looks.

And some people are going to be fine with that, but the majority won’t care for it. They want to know that you care about them for more than their looks. 

Spend some time getting to know them, even if just a little bit before asking them out. Show some interest, ask some questions, be curious. Then, when it's time to ask them out, you'll be able to build on what you already know.

“Hey, you seem rad. I’d love to get to know you more, would you like to (pick something from the list above) with me next week?”

3. Learn To Ask For What You Want...(In Love And In Life)

This is key for everything in life, not just asking people out. Jobs, raises, promotions, getting on Oprah (my lifes goal, obviously). 

Wayne Gretzky said you miss 100% of the shots you don’t take. I trust him, look at his hair.

There’s nothing sexier than a confident person who can ask for what they want.

If you want to go on a date with someone, say it.

"Hey, would you like to go on a date, with me?”

Now it’s clear as day that you’re interested in a date. No more first date ambiguity. No more guessing if the coffee you’re having is a friendly coffee or a romantic coffee. 

I love all coffee, but I especially love romantic coffees!

4. Don’t Take It Personally

Rejection is not personal, no matter how personal it might feel. When people say no to you asking them out, they’re simply expressing a preference, and unfortunately you’re not it.

It’s not even worth asking why. It could be that they’re not available, recovering from a breakup, not attracted to your gender, or, gasp, just not interested in you!

Life is too short and there are too many people in this world to get bent out of shape over one rejection.

Need Tips On Handling Rejection Like a Freaking Ninja?

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Oh, and no means no. Some people have been taught to become more persistent when faced with rejection. That may be applicable for a promotion, but there's no room for it in dating. 

Being Open, Kind, and Playful Never Hurt Anyone

Not once, not ever.

These upgrades are designed to help you become more open, kind, and playful. These are the keys to having more intimate, connected relationships, and to driving more love to your life.

So next time you're tempted to ask someone to hang out, challenge yourself to get to know them a little bit, and invite them to something fun. Play with them, and interact with them in the larger context of the world.

And when someone says no, take it graciously and move on.

Life is short and it's a beautiful day out. Go enjoy it. 

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Shaun Galanos

Shaun Galanos is a love coach and host of The Love Drive podcast. His mission is to spread love through emotional intimacy. He lives in Montreal with his dog, Roger.