If you find it hard to choose the right moment, or if you do not know what to talk about, these tips may help.

When is the right time?
When is the right time to approach someone you like? If you are sure you will see them again (for example, because you go to the same school or go to the same club every Friday), you can take more time than if you are completely taken with them the first time you see them and have no idea whether you will ever see them again.
Give yourself time to flirt
If you take a little time before approaching them, you could flirt with them first. Flirting is a game you can play together without words. If they respond to your flirting and play along, they will probably start to want you to approach them.
Don’t wait too long
Of course, taking too much time does not help either. If you start to suffer because you do not dare to approach someone, it is best to put an end to that suffering quickly. You can also wait for them to approach you. But maybe they are just as shy as you are — and in the end, no one talks. That would be a shame. If it feels very hard to start talking, we recommend doing something that helps you like yourself more and feel more confident. Then take a brave step toward them — because what do you have to lose?
Picture the conversation beforehand
It can help to imagine before the conversation what you want to say to them, what questions you want to ask, and how you might answer their questions. It is a good idea to do this in the evening before you fall asleep. Things we picture or think through right before falling asleep tend to stick in our memory better.
How can I start a conversation?
You could greet them with “Hi, my name is…” or “I see you here a lot.” It does not matter that much what you say. If someone wants to get to know you, they will also help make sure a small conversation develops. You can look around and notice what is happening around you. Then you can start with a comment about something you see or hear. This lets you begin talking in a relaxed, low-pressure way and break the ice.
If you cannot speak because of a disability, or if you use sign language, you can still start a conversation. You could write a note or type something on your phone and explain that you need another way to communicate, but that you would like to talk.
Don’t be too direct
If you want to have sex with this person or you are in love with them, it is usually not a good idea to be too direct right away and surprise them with “I’d like to have sex with you” or “I love you.” They may need more time to develop more interest in you and to imagine being with you. So it is better to take it more slowly and get to know them a little first.
Show interest
When you talk to someone, they should feel that you are interested in them. If you just talk on and on, they will not get that feeling. On the other hand, they probably will not like it much either if you only question them and do not share anything about yourself. It is best to first say a little about yourself and then ask how it is for them. For example: “I like coming here in the evenings because it helps me unwind. During the day, I’m usually pretty stressed. What about you?”
Be open
It usually comes across well when you talk about yourself honestly, instead of making something up just because it sounds good. People with strengths and weaknesses are more likable than people who act full of themselves or brag. After all, the people you want to win over have weaknesses too. And when you talk about yourself honestly, you show courage. This also makes it easier for the other person to open up.
Handle silence
Of course, it can happen that you suddenly do not know what to say anymore. Then do not try too hard to say just anything. Let the silence be there for a moment. Focus on your belly breathing. This can calm you down. And open your eyes and ears. What is happening around you? Maybe you will notice something you could talk about. You can also mention the silence: “Sometimes I don’t know what to say. My mind feels empty. That’s annoying. Tonight in bed, I’ll probably think of what I really wanted to talk to you about.” This will probably help you break the ice again.
Be clear
When the time comes to tell them how you feel, it is best to be clear instead of vague. “Can I kiss you?” or “Do you want to be my girlfriend/boyfriend?” is clearer than “Should we give this a try?” or “How about the two of us?”. The more clearly you say what you think and want, the fewer misunderstandings there will be.
Practice, practice, practice
When you try approaching different people you like and practice doing it, you are more likely to find your own style. And what takes a huge amount of courage at first becomes easier with more experience. It is also important to experience that you may get turned down sometimes. Everyone has this experience. Even the very best seducers. Don’t let it throw you off. Look for someone else you like.