In keeping with this month’s theme of the empowerment of women, because March is women’s month, I decided to look at one specific aspect of our lives as females, and that’s dating. Many of us have partnered up and are pretty happy in our relationships. Others who are looking to change their relationship status, why not take advantage of this historic month and make the first move?

Okay, so maybe you feel a little bit uncomfortable with the idea. I can definitely understand why. We’re used to the traditional way that dating and courtship are carried out. That is, the man makes the first move, and if the woman is interested, she responds positively.

This is all well and good, but it does involve a certain amount of waiting. However, some of us may be beginning to feel that we don’t necessarily want to wait, right?

What if the guy we’re interested in is actually interested back, but needs a gentle nudge in our direction? Maybe he’s waiting for you.

Time to assert our agency, ladies. We no longer live in the olden days of having to wait around. I’ve made a list of surefire ways of making the first move, and the rest is up to the object of your affection.

After all, what’s the worst that can happen? You could find out that he’s not into you, and that’s perfectly all right. We have the freedom to be attracted to who we choose.

But at the very least, you’ll know for sure. And what’s the opposite of that? Number one, wondering if something beautiful could have happened between you. And number two, regretting that you never took the chance to find out.

Ways to make the first move

1. Type your contact information into his phone.

Let’s say you strike up a great conversation with a guy you meet at a party or at an event. You hit it off pretty well, find out you have a lot of things in common, and the evening ends but you just know you’d like to see him again to find out where things might go.

Our smartphones are always with us these days, am I right? At the end of your time together, ask to borrow his phone. Write down your phone number and your name with a short descriptor (+65 XXXX XXXX ‘Rachel—biggest Harry Potter fan next to you’, or Emily—loves 80s music). Something that will make him smile every time he sees it.

This is pretty bold, I know. But sometimes you just have to go for it.

2. Slide into his inbox with a conversation starter

Ahhh, social media, what did we ever do without you? Everybody can send messages to the people they meet and friend or follow across different platforms.

So you meet someone, and you think they’re attractive, and you want a chance to get to know them better. Send them something—a link to something you have in common, or had a conversation about. An interesting quiz. A gif that you know will make them laugh. A video of a cat playing the piano.

This sends the message that you want to keep the conversation going. And if he feels the same way, he’ll bite.

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3. Ask him out on your birthday or any other special occasion

If you are hoping to take a friendship with a guy to the next level, wait for a special occasion and then take advantage of it by asking him out.

It will be very hard for him to say no to you on your birthday or an occasion like a good friend’s wedding or your grandparents’ golden anniversary, wherein you need a plus one for the celebration.

Who knows, you might start out as friends, and end up as something more. After all, you have each other’s undivided attention for at least a few hours and it’s a perfect opportunity to get to know each other well.

Hmmm, let me press pause for a moment here. Suppose you’re interested in someone, but his money habits have left you a little concerned. I have just a think that will help you. Hop on over to What to Look Out For: The Top Financial Red Flags in Dating

4. Enlist your friends and go out on a group date

This is one of the oldest ways to get to know a guy you’re interested in a little bit better. After all, what are besties for? Tell a few of your friends that you’re interested in someone, and you’d like an opportunity to spend some time with him.

Get a group together, maybe not too big of a group so that it’s easy to break off into smaller conversations, but it shouldn’t just be you, your BFF, and the guy either, since that could turn out to be quite awkward.

Let it be a few couples and singles getting together, it could be for a movie or a concert, or a quick trip to the beach, or a meal together, A casual setting where there isn’t a lot of pressure should give you a chance to get to spend some quality time with the guy you have your eye on.

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5. Use the “I have an extra ticket” gambit

Also an old and tried and tested method that works like a charm. Let’s say you just happen to buy an extra ticket to an event that you know he’d be interested in. What better way to get together than to invite him to come with you?

He’ll be grateful, which will put him in a good mood. And you’ll have the advantage of having him all to yourself for a good few hours and seeing where it goes from there. You can even extend the evening by asking him out for a drink or some coffee or even a meal, afterward. Why not? You ’re already out, you may as well make the most of it.

Just do it.

Of course, you’ll feel nervous and uncertain at the start. Nobody wants to feel rejected as they put themselves out there but the object of their affection didn’t feel the same way.

But, this happens to everyone. We all have to face this in one way or another. And we can’t take it personally, but we have to know that when a guy doesn’t like us back, it’s not a reflection on our character. It doesn’t mean it’s because of our shortcomings or flaws. The heart, as they say, simply wants what it wants.

But it’s 2019 and we have a choice to live as empowered women who step out and go after what we want. Trust me, this is a wonderful way to live!

Needing more relationship tips? I’ve got the perfect article for you right here How savvy women make smart relationship choices. You’re welcome!

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Founder @ The New Savvy
Anna Haotanto is the Advisor (former CEO) of The New Savvy. She is currently the COO of ABZD Capital and the CMO of Gourmet Food Holdings, an investment firm focusing on opportunities in the global F&B industry. She is part of the founding committee of the Singapore FinTech Association and heads the Women In FinTech and Partnership Committee. Anna is the President of the Singapore Management University Women Alumni. Anna invests and sits on the board of a few startups. Anna is also part of the Singapore Chinese Chamber of Commerce & Industry Career Women’s Group executive committee. Anna’s story is featured on Millionaire Minds on Channel NewsAsia. She hosts TV shows and events, namely for Channel NewsAsia’s “The Millennial Investor” and “Challenge Tomorrow”, a FinTech documentary. Anna was awarded “Her Times Youth Award” at the Rising50 Women Empowerment Gala, organised by the Indonesian Embassy of Singapore. The award was presented by His Excellency Ngurah Swajaya. She was also awarded Founder of the Year for ASEAN Rice Bowl Startup Awards. She was also awarded the Women Empowerment Award by the Asian Business & Social Forum. Anna has been awarded LinkedIn Power Profiles for founders (2018, 2017), Tatler Gen T, The Peak’s Trailblazers under 40 and a nominee for the Women of The Future award by Aviva


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