How To Flirt With A Shy Guy Who’s Too Timid To Ask You Out Himself

Not to sound too biased, but guys who tend to be shy and reserved usually make good boyfriends. I know this because I’m pretty shy myself.  Most of us are genuinely nice guys who know how to treat a lady right. Of course, the problem is getting the ball rolling. Shy guys aren’t extroverts who will start a conversation out of thin air and we aren’t always great at flirting. Also, some of your usual flirtatious ways may not work with us. However, there are ways to get us to come out of our shells. Here are some things you could try.

  1. Make the first move. Sorry, ladies, but you’re usually going to have to make the first move with a shy guy. A lot of us don’t have a ton of confidence when it comes to women. It’s also not in our nature to be outgoing and come to you first. If nothing else, you’re going to have to hint really hard that you’d like him to strike up a conversation and start flirting with you.
  2. Make sure he’s alone. Shy guys don’t like large groups of people and we usually don’t like an audience. We also get nervous when it feels like we’re the center of attention. That’s why it’s best to get him alone so he’s not worried about other people overhearing the conversation. Even if his friends are around, he’ll feel nervous or embarrassed if you try to flirt with him with other people around.
  3. Only ask open-ended questions. While it seems a little counterintuitive, you should try asking as few questions as possible when trying to flirt with a shy guy. At the very least, avoid questions with a one-word response and keep them open-ended. This is the best way to get a shy guy to open up and start talking more, especially if you can find a topic that interests him.
  4. Ask for his help with something. This is a perfect ice-breaker with shy guys because most of us are nice and willing to help if you ask for it. It doesn’t have to be a huge favor or anything big. Frankly, you’re just looking for a way to break the ice and get him to start talking to you without coming on too strong.
  5. Act a little shy yourself. Sure, it’s true that opposites attract and some shy guys might prefer someone who’s a little more outgoing. But you don’t want to be too outgoing or have too much energy when trying to flirt with a shy guy. If you seem loud and wild, he may not respond to that. You want to come across as calm and quiet and a little guarded as well. He’ll be able to relate to this and feel a little more comfortable when he realizes that you’re trying to flirt with him.
  6. Don’t tease him. This might be your go-to move when flirting, but teasing isn’t going to help with a shy guy. We may not recognize right away that you’re trying to flirt with us. We’ll just think that you’re being a little mean, even if you think you’re being playful. At the very least, we’ll feel a little uncomfortable. At least at the beginning, avoid any teasing and just be nice to him.
  7. Just smile. It may sound overly simplistic, but this can be effective with a shy guy. Most of us love being around a woman who has a nice smile, and so we’ll respond positively to that. Just talk calmly with a guy while smiling at him a lot. It’s a great way to at least hint that you’re interested without coming on too strong.
  8. Listen. While you might need to do a lot of the talking early on, once you get a shy guy talking, just listening and smiling can be a good way of flirting. You’ll want to get him to open up by having him talk about something that he likes, but you also have to show him that you’re listening. If you don’t, he won’t think that you’re interested and he won’t respond to any flirtatious vibes you send his way.
  9. Break the touch barrier. A shy guy probably won’t do this on his own, so you’ll have to be the first one to break the touch barrier. Just make sure that you’re not too aggressive. Ease into it with something harmless and unassuming. It’ll help send the message that you’re trying to flirt with him without coming on too strong and overwhelming him.
  10. Make it clear you want to see him again. You can’t always assume that a shy guy will ask you out or ask for your number right away. Without being too obvious about it, think of a reason why the two of you should exchange numbers. You can also let him know that it’d be nice to see him or talk to him again. Try to think of a situation in which the two of you might spend time together again and see if he responds positively. This may not sound like the most conventional form of flirting, but it can be a good way to show your interest and get the ball moving with a shy guy.
Bryan Zarpentine graduated from Syracuse University and lives in upstate New York, where he writes largely about the world of sports. His work has appeared on Franchise Sports and WSN, among others. You can find him on Twitter @BZarp.