When initiating a conversation with a guy in person for the first time, it’s important to be authentic, confident, and engaging.

Be yourself: Don’t try to be someone you’re not. Authenticity is key to making a genuine connection.
Comfort: Focus on feeling safe and comfortable in your body. If you tend to feel nervous, take deep breaths to relax your shoulders, neck and jaw.
Start with curiosity: Instead of assuming you know what a guy is thinking or feeling, approach the conversation with genuine curiosity.
Manage expectations: It can take time to meet someone you truly connect with, and there are no guarantees. Don’t get discouraged if it takes longer than you’d like.
Avoid neediness: Do not make it seem like you need this person to fill your needs.

1. Approaching Him

Strategic positioning: Position yourself where interactions are likely, like a communal table or near the counter at a coffee shop.
Be yourself: Do not strategize to get someone to like you. Instead, show up authentically.
Eye contact and a smile: Sometimes, it doesn’t even require words. Eye contact and a genuine smile are great ways to start an interaction based on a shared experience. You’re creating an invitation for engagement, signalling warmth and approachability.
Don’t overthink it: Try not to strategize or overcompensate. Leave your confirmation bias at the door.

2. Starting the Conversation

Simple greeting: Begin with a simple and friendly greeting, such as “Hi” or “Hey”.
Be direct: It can be refreshing to be direct and honest. For example, you could say, “I’d love to pick your brain on something,” or, “I’d love to have coffee with you”.
Compliment: A genuine compliment can be a great way to break the ice, such as “I think you’re really cute” or “I find you really interesting”.
Reference your surroundings: Instead of relying on pre-planned conversation starters, notice what’s happening around you. If you are in a coffee shop, you could make a comment about the coffee, or about something you have in common. This provides a natural, unforced way to initiate communication, moving away from the pressure of ‘performance’ conversation and into a more spontaneous, organic approach.
Do not overdo it: After you present your interest, do not feel you have to do anything more. If he is genuinely interested, he will make an effort to pursue you.

Be a good listener: Focus on active listening, asking follow-up questions to show your interest. Be sure that you are listening to understand, not to reply.
Be engaging: Be warm, expressive, and enthusiastic.
Flirtatious energy: Flirting includes giving a little compliment, making more eye contact, or giving a look that communicates you are interested in more than just the conversation.
Show curiosity: Ask questions that show you are genuinely interested in his thoughts and feelings.
Share about yourself: Offer some information about yourself to create a two-way interaction.
Normalise vulnerability: Don’t hide any nerves during the conversation. This will help to make a guy feel reflaxed and able to share his thoughts and feelings.

Serious topics: Don’t rush into serious topics or try to force a connection. The first interaction is about building rapport, so keep it light.
Don’t overdo it: Don’t be too eager or overly complimentary.
Do not chase someone who is not interested: Chasing can make the other person feel uncomfortable and create an imbalance of power. When you are chasing someone, you are crossing boundaries.
Negative comments: Avoid making negative comments or judging.

How you feel: Pay attention to how you feel when you are with him. A relationships need to be built on a foundation of feeling good about yourself and the other person.
Rejection: It is important to change your relationship to rejection. Don’t take it personally; move on to the next person if you get rejected.
Be proactive: Don’t wait for him to make the first move. Take the initiative and reach out to him.
Exchange contact information: If the conversation goes well, you can suggest exchanging numbers or social media. However, don’t get caught up in “researching” someone online before you decide whether to see them again.
Suggest a date: You can directly ask him out, or keep it light by saying, “I’d love to pick your brain on something”.