How to Start a Conversation with a Guy

Attempting to start a conversation with a man can be daunting, but it doesn’t have to be. These conversation-starters will help out!
How to Start a Conversation with a Guy

We ladies tend to enjoy talking. But how do you start a conversation with someone new and make that oh-so-important first impression? We all know the tried and true “Some weather we’re having,” but can’t we do better than that, for God’s sake?

Attempting to initiate a conversation with a man can be daunting, but it doesn’t have to be. In fact, starting a conversation with a man can be fun! The following conversation-starters should get things flowing in a unique and clever way. Just remember to be your authentic self (aka, don’t try too hard), make eye contact, and smile.

Start a Conversation with These Tips:

1. Introduce Yourself

Introducing yourself is pretty straightforward, plus it shows you have confidence – which is attractive. Just shore yourself up, walk over to the guy, and say something like, “Hi. Do I know you? I’m Kathleen.” At this point, he should respond with his own name (And if he doesn’t, he’s a dolt. Swipe left). Make sure to repeat his name during your exchange. Using a man’s name in a conversation tells him that you’re interested and that he’s memorable. This nudges him to remember you as well.

2. Pay Him a Compliment

An enthusiastic and sincere compliment is a sure-fire heart-melter that calls for a response. Maybe he’s wearing a vintage band T-shirt, “I love your shirt.” Or, “OMG, you smell so good. What cologne are you wearing?” Or better yet, compliment his dog. “Your dog is so beautiful. What breed is he?” Boom! You’ve got him.

How to Start a Conversation with a Man

3. Ask For Help

Men love to help women. And, frankly, we could use the help sometimes. Something as simple as “Can I borrow a pen?” will bring an opening to connect. Even better, appeal to his “he-man” strength (and yes, we know you don’t need his help) if you want to give him a confidence boost. When you’re struggling with those groceries or that big box you’re trying to carry into the UPS store, “Would you hold the door for me?” is impossible to ignore. And if he has manners, he will not only hold the door, but he’ll also offer to carry the box. Of course, always make sure to say “Thank you.” Show him your manners and your pearly whites as well.

4. Questions

Some people can be a little, how shall I say – dense. If this is the case, try helping him out. Questions are great conversation starters. Remember that vintage band T-shirt you complimented him on? Ask him where he got it!

Asking for an opinion or recommendation is tried and true. You spot a high-quality man at a bookstore. “I need to buy my brother a book for his birthday. Any suggestions?” Open-ended questions demand longer answers, whereas a “yes or no” answer will kill your conversation in one syllable. “Either/or” questions generally require more than monosyllabic answers. Posing a thought-provoking question will show him how smart you are. Asking questions about him should lead to him asking questions about you. And if it doesn’t, if he yammers on and on about himself, you don’t want him.

5. Pick Up on His Interests

That good ol’ vintage band T-shirt, “I love that band.” Or if he has a surfboard strapped to his car, “Did you get in the water today? How was it?” He’s wearing a ski jacket with a raccoon-eyes tan on his face. “How was skiing?” (A little humor goes a long way).

Starting a Conversation with a Guy

6. Comment on Your Surroundings

Check out your environment, and bring up something you both can relate to. The restaurant’s ambiance, the club’s loudness, the symphony you’re seeing, or… okay, okay, okay – the weather. “Oh, my gosh, it’s hot out. I’m melting.” With a dose of your delightful personality, it could be a good icebreaker. Once you get the conversation going, step back and let him do his thing. Guys tend to like the sound of their own voices. And if you can get him talking about himself, you’re

7. Listen!

Couple chatting on the couch; conversation

The real key to starting a conversation with a man (or any conversation) is to listen – really listen to what he’s saying. Not only is it good manners, but it will also build his confidence. Let him know what he says matters, and show you are interested in him.

8. Know When to End

Finally, one of the most important parts of conversing with a man is knowing when to stop talking. Sure, you may think you know how to start a good conversation, but do you know how to end a conversation without it being awkward? Gracefully exit your conversation early enough to leave him wanting more, “I probably should get going now. I have an appointment.” And if you are feeling confident, slip him your number or business card. Who knows, this may be the beginning of a beautiful relationship.

Now get out there and start a conversation with someone new!

Read More:

13 Fun Indoor Date Ideas

Getting a Second Date: 14 Tips

How to Have Difficult—But Necessary—Conversations


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