One of my readers a while back asked me this question.

Q: Hey Steven, I like this girl but she’s really shy and she doesn’t talk very much to anyone. How should I approach her to be my girlfriend?

So you meet a cute girl, but the problem is that she’s too shy! You have no idea whether she likes you or if she just wants to be left alone.

Shy girls can be tough to crack. A lot of times guys might just simply give up because they think that the girl isn’t interested in them or just is too boring. Actually it’s not true. Shy girls can be very interesting, you just need to know how to crack their exterior and make them open up.

I recall one time I dated a very shy girl. My first impression was “Oh, she’s not interested in me.” I was my usual charming self but she didn’t seem to reciprocate very well. She was quiet and during our date in the early stages it was slightly awkward because I was doing most of the talking and she wasn’t giving me much chit-chat. I persevered and asked her out again and she said yes. Later on she told me that she was incredibly attracted to me, but she just didn’t know what to say because she was nervous talking to me. Of course after dating me, she was no longer shy around me (although she was still shy around others). This was one of my best long term relationships and lasted quite a long time before we called it quits due to long distance.

Here are my 7 tips to help you maximize your chances with that very shy girl.

Tip #1) Activity-based dates – Go on dates where you guys actually can do something instead of where you have to continue talking for a long time. For example, going to dinner probably isn’t a good idea because it might feel incredibly awkward for both parties. Instead go on a date where you can play something or do something. For example, play tennis. Go shopping. Go rock climbing. Find an activity where you don’t need to be talking 24/7.

Tip #2) Finding commonalities – Some say opposites attract, but I say alikes attract. If you can make her feel that she isn’t so different from you, then she is going to open up. If you find a topic of interest that both of you can talk about, then you’re going to be golden for conversation. For example, try talking to her about a movie that she likes or particular genres that she likes (maybe you both like chick flicks). Perhaps ask about what she studied in College or what she does for fun and see if any of your hobbies align. You’re going to find that both of you will open up when you realize that you two aren’t so different.

Tip #3) Asking questions instead of saying statements – In normal conversation it is common for us to simply make statements and expect the other person to comment on them. For example, I might say something like, “Wow the weather is really nice!” and then my friend might say “Yeah! It’s perfect weather to play outside.” You’ll notice that we both contributed to the conversation without any questions being asked. Shy people won’t always engage themselves in conversation. Make it easy for her. Instead you should continually ask her questions to get her engaged into the conversation. So instead of “Wow the weather is nice!” say, “Don’t you like the weather we’re having?”

Tip #4) Don’t convey awkwardness – She’s already being slightly awkward, so if you contribute more to the awkwardness then it’s going to be intensely uncomfortable for her. Realize that she is probably super nervous talking to you. What you need to do is even if there are silences in conversation, look aloof, look happy. Don’t let your face seem nervous. If she sees that you seem to be ok with the silence, then she is going to feel ok about it also. Make her relaxed with you and keep the interactions loose to get her more comfortable expressing herself.

Tip #5) Sharing Funny/Embarrassing Secrets – The more you reveal about yourself, the more likely she will reveal details about herself. This means that you should think about the most embarrassing things you’ve done and tell her without batting an eye. Of course, don’t pick things that will make you look like a douchebag (ie – “I went out and got rejected by 20 women last night at the club”), but tell her things like funny stories about your past experiences (“I went to school one day and my pants ripped, leaving a huge hole in my crotch area”). Telling her funny, embarrassing secrets about herself both lightens the mood and makes her feel like she can trust you because you trusted her with your embarrassing experience.

Tip #6) Always be leading – With shy girls, you’re going to always be leading the interaction and the relationship. You are always going to be making the decisions. So don’t make it hard on her by being indecisive. As a man you should know what you want. Have an attractive alpha personality. If she asks you where you’re going for dinner don’t say, “Hmmm, I don’t know, you pick.” She doesn’t want to pick. She wants you to pick. Why else would she have asked. Don’t expect her to make the first move. You must make the first move. This means YOU have to go in for the kiss. YOU have to get her in bed.

Tip #7) More obvious flirting – If a girl has less social skills, it’s up to you to really flirt with her. Like AMP it up. You don’t need to be giving her subtle hints and hoping she picks them up and reciprocates. You need to be saying stuff like, “Hey, you’re cute as hell right now” or “Trying to impress me with that sexy outfit huh? I like it.” Don’t do this immediately, but after you guys are more comfortable talking to each other then you really need to make it obvious that you do like her. So try this on probably the second or third date or so. The first date is too early for these kind of comments and they can make her uncomfortable. You are a stranger after all.

Of course even after all these tips, it will still take some guts and perseverance on your part. You can’t just give up even if things look grim. So gather up your courage and ask that cute shy girl out on a date and see where it leads.

Keep the questions coming. Send me an e-mail at steven_lin AT ampedasia.com.

If you’re an Asian man desperately seeking love advice, you need to check out my free tips on my website, Advanced Asian. And if you sign up for my mailing list (or Amped Asia’s list) you are going to get a free e-book entitled Asian Men: Advance Your Dating Life that could potentially change your love life forever.

Written by Steven Lin