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Tough Love Questions: How to Make The First Move?

how to make the first move

Read any guide to being a Modern Woman, and it’s sure to be replete with mantras on leaning in, taking charge, and breaking down traditional gender stereotypes. Yet, while we celebrate our girlfriend’s climb onto the latest rung of her career ladder, we’re still gasping in surprise when she tells us she made the first move on a date. Should we really, though? 

Instead of abiding by the oh-so-romantic traditions of staring daggers at the back of your crush in hopes of making eye contact, waiting by the phone with gripping anxiety for him to initiate a text conversation, or feigning complete disinterest just to play “hard to get” — which frankly, only serves us helpings of ice cream binges, helplessness, and misery. You could instead take power into your own hands and be the romantic pursuer instead. After all, a modern woman deserves a modern romance. 

How then, can you make the first move on that romantic interest of yours? We’ve broken it down into 3 baby steps for you:  

1. Read the signs first

how to make the first move

Look both ways before you cross the metaphorical love street. Before you decide to ask someone out on a romantic date, make sure to observe signs or hints the other party might be giving that would indicate he’s interested too.

If it’s someone new: You probably don’t know much about them, so look out for possible signs that they are single. Friendliness can sometimes be mistaken for flirting. So be sure they are available before jumping at the opportunity.

If it’s someone you already know: It’s always easier to ask someone out when you already know and trust them. Look out for signs by observing the differences in their body language with you, and with their other female friends. If they’re showing more interest or giving you more attention than others, it might be a green light to make a move.

Typically, when we’re attracted to someone, we tend to lean in towards them when speaking, mirroring our body language to theirs, or make light physical contact, such as a casual touch on the arm while chatting. So if your romantic interest checks all these boxes, you’re on to the next step!

2. Be bold but casual 

Nerves can get the better of you when you’re asking someone out for the very first time! The good news is you don’t have to make any grand romantic gestures. The trick is just to be your casual self, with an extra splash of confidence. 

If it’s someone new: Drop a casual compliment if you have to break the ice, and make some small talk to find some common interests. If the conversation’s going well, it’s the perfect time to ask for his number or chat more over a meal or drinks!  

If it’s someone you already know: If you’re currently friends with your romantic interest, being casual should come naturally to you already. What’s left is just to ask him out on a one-to-one date!

3. Ask them out on a date

Once you feel comfortable with the progression of your first move, don’t be shy to ask them out. 

When you’ve already established some common interests both of you have, it’ll be much easier to plan date ideas. Do both of you love Japanese cuisine? Casually suggest checking out that new Japanese restaurant together. Asking him out with an activity he’s sure to enjoy will get you one foot in the door. 

If you’re still not comfortable being alone, plan for a double-date with a friend you can rely on. You’ll find it easier to be yourself. 

Here are some activities we recommend and outfits you can consider for your first outing:

  • Dinner Date:  A classic date idea that never fails. You can indulge in conversations and get to know each other a little more in an intimate setting.
how to make the first move

Rent from the Infinite Wardrobe: Raquel Jumpsuit by Unitedwood and Lady Dior

  • Sunday Brunch: Who doesn’t like coffee and a brunch menu? Brunches are great for first dates, as you can still plan for more activities after brunch if the date’s going well. 
  • Movie Night:A good option if you’re not much of a talker, or if you’re feeling shy. Pick a movie that you’re both able to enjoy and bond over it after! 


  • Music Festival or Concerts: This option is not just fun but it helps you loosen up once the music starts playing! In addition, you get to know each other’s likes and dislikes in music. 

Ready to make your first move yet?  The best that could happen is a budding romance you won’t forget. The worst? You’ll meet with rejection, but learn a few things about yourself – which isn’t so bad either. There isn’t a definitive playbook, so make your own rules and own it — you never know what fruit your boldness might bear. 

Read more on other tough love questions.

About Author

Ashley is fun-loving, and pens down anything that’s got to do with food, fashion, and films. She occasionally indulges in pop-culture narratives and secretly loves FPS games (betcha she can beat you in it!) Nothing excites her more than a trip with a scenic view -- mountains and fjords included. Her favourite apparel piece is a skirt, for it's flexible and flatters her height-- an added bonus if it comes with pockets!

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