Dear Ms. Wai – Making the First Move

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I’ve read your past columns about girls needing to be more brave and making the first move. I’m okay with doing that but….how? Previously guys have always made the first move. Now that I want to make the first move I’m not sure how to go about it?

For instance yesterday I ended up meeting a guy (a friend of a friend) and we got along so great. The mutual friend had to suddenly leave early and me and this guy ended up talking (and drinking tea) for hours.

So what do I do now? How do I show him I’m interested without coming off as desperate? I have his WeChat and I want to ask him out for dinner tonight and keep talking but is that moving too quick? We really hit it off, but he hasn’t written to me yet and I don’t know what he thought about last night. Should I not “contact him for three days” or whatever it is that pick-up artists tell men to do for women? Thanks for the help!


Hey Sara,

Glad you are taking destiny in your own hands and realizing that it’s okay to make the first move. Girl power! *Fist bump*

Although, it’s true. If you don’t have any practice in it, how do you make the first move? Boys kinda figure this out in high school and college, but girl’s tend to have less real life experience being the pursuer.

I think by nature the girl’s approach is going to be different. Girls tend to not saddle up to a guy and put their arm around them with their other hand holding a beer at some club. (Not that a woman couldn’t do that.) We tend to be less obvious and less physical in our flirtations. Like you said, you had so much fun talking to him. While I’m sure a part of you wanted his hot body and sexy face, you didn’t write that in your letter which leads me to believe you are attracted to his personality above all.

How to make the first move?

So maybe take it a little slow. Those “don’t contact a girl for three days” rules are old fashioned. Nowadays, with instant communication you should contact him. But since it is a new friendship, don’t contact him just to say “hi.” You can run out of juice quickly and the conversation can turn trite and boring. (“Sooo…what did you do today?” “Nothing much, you?” “Just woke up.” Boring!)

Instead contact him when you have something to say that will start a conversation. Did you talk about a book or a movie or some past travel experiences or something? Bring that up again but with new information, like a picture of the book you recommended, or something you got from your travels in said place. Something to re-ignite the conversation but with a new aspect to keep it fresh. Also, when the conversation seems to be running a little thin, say you have to go and give the conversation a clear stopping point or it will just awkwardly go on with long pauses forever. Everyone gets tired of that.

But all chat and no play makes Jill a dull girl. You’ll need to work a date into the conversation somehow. I can see one opening, depending on how good a friend the “mutual friend” is. Since your friend had to leave unexpectedly maybe make another threesome date and ask your friend not to show.

Or did you talk about some restaurant or kind of food? Ask him to show you something he recommended or invite him to try something you talked about. Admittedly it is still a bit vague and he, and you, will still be unsure of the others feelings, but its a place to start and you can grow from there.

Of course, the quickest and surest way to find out is to lay it all out on the line and just say your feelings. “I had a really great time the other night and I feel like you are someone I can get very close to. Would you like to go on a date and see what happens? How about Friday night?”

Of course this takes a lot of courage. Saying it face-to-face is the best, but very hard. So use WeChat, type it out real fast and send before you have time to think about it. Then wait in agony for a reply which could be hours in coming.

Personally, I have no patience and a low embarrassment meter, so I have done this method several times with pretty good results. One guy made me wait an entire day before he answered. He wanted to say yes but thought I was actually making fun of him because “why would a foreign girl like me?!'” Sigh. Luckily I kept chatting with him in a relaxed breezy manner that night and when I brought it up again, he admitted he liked me too.

But be prepared for devastation. I once told a guy face-to-face. We were hanging out, talking about friends and I said something about how I would like to be more than friends. So I asked him, “Are you interested in more than friends?”

“No,” was his immediate answer. Crushed and humiliated, I sucked it up. “Okay then. Just friends. But good friends.”

“Yeah,” he said, feeling embarrassed. “Good friends.”

The thing was I kept hanging out with him and chatting like nothing happened and we actually did become good friends. We ended up being roommates for a summer and he even came to America with me to meet my family, all platonic. It took me a few months to get over him, but I acted like everything was normal. After all, if I liked him enough to be my boyfriend, of course I’d like to be his friend. He later said if I had acted embarrassed or pulled away, he wouldn’t have reached out because he didn’t want to hurt me anymore. Lucky for both of us I didn’t. But again, I had to be the aggressor even in friendship.

I hope that has given you some ideas. Be cool about it, don’t WeChat him obsessively, or ask him out every night. Take it a little slow, but try keeping it moving towards your objective of an obvious date or a declaration of feelings. And hopefully at some point, he should take over the pursuit.

This might not come natural to you as it is your first time being the pursuer, but don’t let that frighten you off. Just see it as a new experience which could lead to some excellent results. And even if it doesn’t work out and he refuses you, you have stretched your courage a little bit more and that will help you in life. Good luck!

If you have a question for Ms. Wai ask in the comments below or send an e-mail to

Ms Wai

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