6 Secrets for How to Start a Conversation with a Guy that He’ll Love

Have you ever had a good-looking, really cool male friend that you want to date, but you can’t seem to get a conversation started? Everyone just tells you to go talk to him, but sometimes that’s easier said than done!

What if the situation is awkward or if you don’t really have a lot of time to chitchat? After all, real life isn’t like Friends. Not everyone’s in a diner just waiting for a full conversation. People are in a hurry, distracted, and yeah, sometimes not all that friendly. You could say that finding the right timing for a conversation, as well as having the right attitude, is just as important as finding the best topic.

Let’s review six secrets on starting a conversation with a guy that he’s really going to respond to and appreciate. Let’s assume by now he recognizes your face and has already smiled or looked at you. Let’s pick up right at that moment where nervousness and awkwardness starts…

1. Find out his name and use it.

Not only is it difficult to talk to someone without knowing their name, but actually using a man’s name in conversation is an instant “boost” for advancing your friendship. If you don’t know his name ask it. Even if you know it, however, be sure to use it as you look him in the eye. You can even use it a few times during a full conversation. Men like to hear their own name because it makes things more personal. As you become better friends, using his name can even create a feeling of intimacy that leads to intense feelings.

2. Keep things simple.

Don’t psyche yourself out of the moment by over-thinking it. Keep things simple by sticking to something visible or circumstantial. In other words, in the moment. Talking about what’s happening, where you’re at, what’s going on around you, or even something that other people are talking about. This allows you to talk directly to him, or to simply talk to yourself, or other people in general.

It takes the pressure off and lets him respond naturally. The problem some women have is creating a “deep” or funny conversation too soon, when all that’s required at first is just a casual conversation starter. Even something as “what a pretty day” can get a man talking. Use an ice breaker before you talk about anything deep. Think of this as “getting his attention.”

3. Ask an open-ended question.

Another common mistake women make approaching men is asking simple questions, which inevitably leads to awkward tension. Because the answer is always “Yes” or “No” or “Duh!” That immediately sets a strange tone.

Asking open-ended questions, which means they can’t just say yes or no, they have to provide details, or an opinion, put the pressure on them and take it off of you. Asking a question is the easiest way to start an intelligent conversation with a man.

Now don’t over-think the questions. Just because a question is open-ended doesn’t mean it has to be existential, deep or weird. You could ask him about a local event, or a current event happening (especially if it’s playing on TV). Ask him what he’s doing if he’s doing something peculiar. Ask him about the restaurant you’re visiting, or about parking outside, or anything that seems like a simple question that’s not too obvious.

4. Ask for a favor.

You could say that biologically, men are typically very eager to help women. This is so obviously true, that oftentimes sex doesn’t even enter into it. Men are happy to do favors for grannies, children, or even a woman they don’t find attractive. Men want to please other people…and yet they’re especially ready to do a favor for an attractive woman.

Make an appeal to his strength, his ability to provide. Ask him a question and rely on his volunteered knowledge to help you. Ask him a physical favor and let him show off his strength. Ask him about his favorite hobby (if it’s obvious what it is), such as mechanics, music, writing, art, legal work, office work, movies and so on. Be sure to smile and thank him for helping you so he gets the little “reward” that he loves so much.

There…you’ve made a connection with hardly any deep thinking required!

5. Compliment him on something that makes him proud.

Men and women both love compliments…but here’s the catch. People get weird and awkward on compliments that are too obvious (such as handsome or beautiful) or that are out of the blue.

Instead, compliment him for something that he’s doing or has done, to show you’re actually paying attention. This could be his fashion sense, his good work, something he owns or carries with him, or even something he’s listening to. (Such as “Excellent choice…I love this song!”) If he’s walking a dog, compliment his dog. Even complimenting him on his choice of lunch is surprisingly effective, because once again, it shows you’re paying attention.

Should you compliment him on his body or his suit? Sure, but only if he seems to like you. Some men can be put off by such a forward comment, especially if he hasn’t really been staring at you and no friendship has been established.

6. Get a deep conversation going by talking about something you have in common.

Now’s the challenging part. Before you can move on, you must find common ground with this guy. The only reason a conversation can continue is if you both have something in common. So look for something obvious that you can build on.

Where are you? Are you looking for a similar product? Do you like a certain kind of book or movie or type of food? Is he very obviously into sports by what he’s wearing? Even if he’s at work sitting at his desk, you may notice something that shows one of his hobbies. Learn to notice these small details and work them into the conversation.

As you can see the “secret” to a good first conversation is not in being seductive, or quirky or too brainy. It’s just a matter of being friendly and moving at a comfortable pace—his pace, and focusing the attention on him.

About The Author

Matthew Coast

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