How to chat someone up

The thought of chatting someone up can seem very daunting. To some it comes naturally, but to others it is a difficult task. The two key factors to successfully chat someone up are confidence and practice. People make the mistake of using cheesy chat up lines to attract someone, but this is a huge mistake. Chat up lines rarely work and more often than not they leave you looking like a fool. Chatting someone up doesn’t have to be carried out in a bar or club; it can happen absolutely anywhere, on the bus, in a shop, while walking your dog, and many more everyday places. Often, the best chatting up moments occur when you are least expecting it.

Before approaching

Before you approach someone, it is a good idea to look for clues that they are single. A ring on their wedding finger is a definite sign that they are not single, so it is best to avoid chatting them up. Someone without a wedding or engagement ring is a start. Another clue could be what they are doing. If you are shopping in a supermarket, look in their shopping basket or trolley to look for possible clues. If you spy a ready meal for one, then there is a possibility that they are single. Whatever you do, don’t just stare at them. You may be looking for a ring on their finger, or looking hard at their shopping, but they don’t know that. Be discreet and act normally. Make sure you make your move as soon as possible, otherwise the moment may pass and you will have missed the opportunity.

Judge their mood

Once you decide to approach someone, the next important step to take is making a judgement on their mood. There is no point trying to chat someone up who clearly doesn’t want to be. After the initial approach you can usually get vibes from them whether you are welcome there or not. It is vital that you make your judgement quickly. It they don’t appear happy to chat to you, simply move on. There is no point in wasting any time or energy in chatting them up. If they appear keen to talk to you, then casually continue. It is a good idea to match their tone; if they sound happy, you sound happy and if they seem a little sad, don’t try cheering them up, simply lower your voice and match their tone.

The conversation

After the initial “hello” is when most people don’t know what to say. This is the point people use those unnecessary chat up lines. Small talk is sufficient to start off a conversation, so there is no need to have a script prepared. Your location can influence the conversation; for example if you are outdoors walking you can mention the weather, for example “it’s a lovely day today” or “I hope it doesn’t rain”. If you are in the supermarket, you can start a conversation by asking for their advice, even if you don’t need it. You can ask about appropriate wine to have with a certain food, or even ask if they know where a particular item is in the shop. If you find yourself sitting next to someone on the train or the bus who you find attractive, you could comment on the journey, or even the surroundings. Alternatively you could ask them a question about the journey. Simple comments are the best way to start a conversation. If the conversation becomes difficult and you can’t think of things to say, look around you and try to get some inspiration. If you have trouble thinking of small talk, then there is no harm in writing down ideas at home and learning them.


While you are chatting someone up, make sure you pay attention to what they say. This will show that you are taking a real interest in them. Listening to someone is just as important as what you say to them. If you don’t listen to what they say, why should they listen to you? If you feel very comfortable in the situation, make sure you don’t get carried away and end up bragging about yourself. The last thing a stranger wants to hear is you going on and on about yourself. On the other hand, if you are very nervous while talking to someone, take a deep breath and try to relax. You don’t want the person you are with to realise that you are nervous. Try to keep the conversation flowing to distract you from feeling nervous.

Ending the conversation

It is important not to outstay your welcome. If you are chatting to someone on a train or bus, then you can’t always control the amount of time you chat to someone, especially if their stop is before yours. Try not to let the conversation dry up before you depart; if possible leave on a high. Your aim is to leave with a phone number, or possibly arrangements for a date. If you don’t manage to obtain a phone number, don’t worry. The opportunity to chat to someone is a bonus, plus it is possible you will bump into them in the future and have a greater chance of them talking to you. The situation should end positively at a time that seems natural to do so. If they appear to lose interest, it is time to out an end to the chatting up moment. A conversation can be ended easily by saying something such as, “It was nice talking to you, I may see you around”, or “I’ve really enjoyed talking to you, maybe we could do it again some time”. It is acceptable to ask outright if you could have their phone number. If they happily give it to you, then the moment was highly successful and you have no need to worry about your chatting up skills.

An unsuccessful chatting up moment

If the situation doesn’t go as planned, all you can do is walk away. If someone doesn’t wish to engage in conversation with you, don’t waste any time in trying to talk to them. There is a chance they could be in a relationship with someone already, or maybe they aren’t interested in chatting to a stranger. Don’t worry about being rejected; not everyone you approach will want to start a conversation with you. Put it all down to experience and learn from it if possible. If you feel like a meeting has gone well, but they didn’t wish to give you their phone number, don’t be disheartened. Every time you chat someone up, you gain more experience which will hopefully give you the confidence to have many successful chatting up moments.