Conversation Starters for Shy Men: It's All in the Question

One of the hardest parts of being shy is trying to talk to other people. Especially people you like. It took a long time for me to learn how to talk socially to guys, and so I’ll give you a few of the tips I picked up that you can use with women.

Start by asking questions. But not the cheesy questions like ‘Haven’t I seen you some place before?’. They’re pure ‘pick up lines’ and ancient ones at that. Try to avoid ‘pick up lines’ if you can.

The best way to start a conversation is to ask about something in the environment. If you’re listening to music, ask her if she likes it. If you are watching a football game, ask if she's a regular supporter of the team she’s cheering.

If you’re staring at a painting in an art gallery, and she’s doing the same, smile at her and ask her what she thinks. It’s as easy as that!

Always make sure your comments are relevant to your setting. Give your opinion on whatever it is. But keep your opinions mild, just in case you offend her because she’s the artist of the piece of ‘trash’ on the wall!

Using open-ended questions is always the best idea. An open-ended question is one that will get you more than a yes/no or one word answer.

For instance, a closed ended question would be ‘Do you come here often?’ Which allows her to say ‘yes’ or ‘no’ and leaves you in the lurch again, trying to come up with another question.

An open ended question might be. ‘What do you think of this place?’ She can say ‘Nice’ if she’s a shy as you. But it’s more likely she’ll say at least a sentence to answer the question. Open-ended questions usually start with ‘how’ ‘what’ or ‘why’. ‘When’ and ‘where’ usually get you a one or two word reply. But not necessarily.

So a conversation with a stranger might go - ‘What do you think of the band?’ Reply ‘Oh, they’re really good. I always try to get down here when they’re playing.’

You know she likes them now, so you don’t want to say anything too cutting about them. You might simply say something non-commital like ‘I’ve never heard them before. How long have they been around?’

Because you know she’s a real fan, she’ll probably know all about their history. She may tell you this, and you should listen as intently as you can.

Don’t act as if you’re listening, while you’re busily trying to think up your next question. Really listen! This is called ‘active listening’. And if you get really good at it, women will love you for it.

If you’re listening, the pressure is off you a bit. You need only nod your head, make eye contact and ‘hmmm’ in the right places. If she takes a little break, to get your feedback, be ready to add something to the conversation.

It doesn’t have to be much. It might only be an agreement with what she’s been saying. Or a minor disagreement, just to add a bit of spice.

How do you disagree with a woman without putting her off? Find something small that you may not think is quite right and say ‘Yeah, I see your point, but do you really think their sound is original enough to get them a big break?’

You’re not saying they’re crap. You’re just challenging her to defend her opinion with more arguments. She’ll rise to the challenge and give them to you.

If she doesn’t, and something in what you’ve said seems to have upset her, ask her about it. ‘Hey, have I upset you?’ is a good fall-back question. She might not be reacting to anything you’ve said. Who knows, her old boyfriend might have walked in at that moment. You don’t know unless you ask.

Talk about your shared experience, ask her open ended questions and listen to her answers. Before you know it, you’ll feel as if you’ve known her for ever. And maybe your relationship might last forever. Who knows?