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Got something you want to get off your chest? It can be big or small. Either is fine. Get at me here.

I find it difficult to know how or when to strike up a conversation with someone on a night out. Last thing I want to be seen as is pestering or odd etc. How does one approach someone and banish the fear and self doubt?

I think there’s two questions being asked here.

Firstly, how to gauge the reactions of the opposite sex when you meet them in bars, clubs or parties. Generally, this is going to be one of the most challenging ways to get a date with an attractive stranger. Depending on the places you’re frequenting, people may just be there to have fun with their friends and won’t welcome any approach from a stranger.

If striking up a conversation with people on nights out is your primary mode of seeking dates or relationships, I imagine you must be coming up against some serious knock-backs. This won’t be good for your confidence. Try some lower-impact ways of approaching people – such as online dating, hobbies and activities or mutual friends. At least you will have some more grounding with these people, or in the cases of OKCupid or Tinder, you’ll know for sure that they are definitely in the market for being approached by you.

As for knowing when or how to approach a stranger? To be honest, I’d give it one friendly remark and then immediately tap out depending on the response. If in doubt: don’t. If you even get a vague hint of disinterest or awkwardness, abandon ship.

Secondly, there’s the issue of what you describe as “fear and self doubt”. To be honest, I think this is the more pertinent problem. Part of it may be explained by the high stakes manner in which you’re choosing to approach people, but these anxious feelings probably mostly come from within.

Confidence is attractive – and the good thing is that you can learn it. Once you are being friendly, warm, kind and respecting people’s boundaries, lots of people will want to speak to you – and date you too! Play to your strengths. If you’re funny, try and make people laugh. If you’re thoughtful, try to show them this consideration. If you find a topic interesting, find a like-minded soul who would like to talk about it. Know what you’re good at and make it work for you. The more you do this, the better you will get at it. There’s no magic trick to becoming confident except for working at it and knowing your own self-worth.

I think you’ll have a lot more success with dating if you think about it a little more astutely. Bar approaches are a recipe for rejection and alienation, which in turn will increase your self doubt and niggling worry. Reduce the friction and go where people want to be approached, then be sure of how interesting, eligible and delightful you really are. Good luck!

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