Starting a conversation can be a scary thing especially when suffering from social anxiety. The fear of rejection always lingers in the back of the head of our mind and it can be painful when getting rejected. However, there are different ways of approaching people that will reduce the chances of rejection significantly, when applied properly.

Situational Approach

The first way and best way to start conversations is by using the situational context. If you see someone wearing a funny hat, compliment them on how funny you think the hat is. If you see someone listening to music that you like ask them what band it is. This is the least threatening and best way to start a conversation with someone whom you speak to for the first time. The context already explains why you are talking to them without you having to do it yourself. Furthermore, a person wearing a funny hat in public is more than likely open to being complimented on that hat. It would be strange for them to turn around and reject you. The situational conversation starter also sets the tone for the conversation to be continued after the initial topic has ended. The downside for this approach, however, is that not all situations allow themselves to be commented on and that is when the conventional approach comes in handy.

Conventional approach

The conventional approach refers to starting a conversation by asking conventional questions that no one dares to not answer. Examples include: “What time is it? Where is the nearest train station?” In other words, these are questions that we get asked in every day life by strangers who need help. The key thing here to note is anybody in need of help shows a vulnerable side to them and people usually respond well to that. The moral consensus is to respond to someone vulnerable with kindness and support. Upon receiving the help it is important to transition the conversation based on the information given, to prevent it from drying out. For example: “Where is the nearest train station?” “I am not sure let me check.” – proceeds to take out his/her new iPhone 11. “Oh, is this the new iPhone 11, how is it different to the 10? ” This way of starting a conversation comes in handy when wanting to stop someone in their tracks but nothing comes to mind.

Self-directional Approach

The last and most difficult way of starting a conversation is the Self-directed approach. This form of approaching people is similar to the situational approach but the only difference being that this time you are the person wearing the funny hat. In this way, people will look at you and wonder why you may be wearing the funny hat and then you can simply ask “Do you like my hat?” This is very effective because you are warming people up towards you before talking to them. By them trying to reason your actions you are already creating an impression. Let me give you a personal example in a Japanese cafe’. I ordered a super unique dish and two girls who happened to sit on the table next to mine looked at what I ordered and giggled. I started the conversation by asking them “I have no idea how this is going to taste, have you guys tried it before?” This was very non-threatening and got the conversation started. It came to the point where the girls joined our table to continue our general discussion. The self-directed approach is the most rejection proven way of starting a conversation but at the same time very difficult to implement.


Keep these in mind when trying to meet some new people and starting a conversation. The situational approach is the go-to move when starting a conversation if nothing comes to mind use the conventional approach. Occasionally, should the context allow it, use the self-directed approach for it is the one that will get you rejected the least.