How to answer those tricky questions about your past


Most people have questions they hope their date never asks – especially those about past relationships. This is especially true if we feel we made mistakes, hurt other people or behaved less than honourably in our romantic dealings.

Emotions are not rational and all people are capable of behaving in strange ways when they are in relationship – you are no exception. While it would be nice to forget about those instances forever, a date will often be curious about your past because what you tell them can help them decide if you are really someone worth getting to know. Here are four categories of questions which may come up and some strategies for handling them.

Questions about numbers

When a date asks you how many previous relationships you have had it can be just as awkward if you have not had a relationship for a very long time as if you have had a string of bad relationships. A high number could give the impression that you have issues around commitment while too few might indicate a lack of experience. Either way your experience is valid and when doing the math it is probably best to only include significant relationships that lasted 3 months or more.

Your previous relationships were all stepping stones towards the one that is right for you – we learn from every experience, both good and bad, and what your date is really trying to find out is if you are ready for a relationship with them – saying something that reassures them of this is much better than telling them your life story.

As with all personal questions avoid going into too much detail on the first few dates. Wait until you are in an established exclusive couple before you really open up about your personal history, especially to do with exes.

Questions about break-ups

Questions about how come you are single and dating can come up very early on when you are chatting with a match, how you respond can really affect whether the connection between you develops.

The key in answering is to be honest but to keep it very brief and factual rather than using it as an opportunity to share the whole sorry tale – no matter how dramatic or interesting the story might be – even if you think it portrays you in a good light and your ex as the one in the wrong – no date really wants to know all the ins and outs of your break-up.

They are asking to find out that you have some closure around the past and are emotionally available to have a relationship with them. For this to be the case your heart must have healed from being hurt and be free – and trusting – enough for the past not to interfere with you creating a happy future.

Questions about sexuality

All questions regarding sexuality, preferences or values can feel awkward especially if they are asked too soon (avoid asking such questions on a first date). Our sexuality is a sensitive subject and not one you should disclose too much about until you are sure there is a strong connection between you both and a realistic chance of it developing into a healthy relationship. For some people a partner’s sexual preferences, or belief in monogamy, may be essential criteria in order for there to be any possibility of a relationship developing in which case just avoid over-sharing and stick to the facts. More intimate details can be shared when you have become more intimate.

Questions about sexual history

‘When did you lose your virginity?’ is an example of the kind of question you might be asked but also one that can make people feel very awkward fearing they will be judged on their answer. If a date asks any personal question which you don’t feel comfortable talking about it is fine to say so. If you do answer keep it brief and light – many people have funny stories about their first sexual experience but don’t worry if you haven’t, just give the answer that you feel most comfortable with even if that is no answer at all.

With all questions remember that it is not what happened in the past that your date is interested in so much as the possibility of what could happen in the future. Don’t be ashamed of the mistakes you have made but instead share them in a way that shows that you have grown and learnt from the experience.

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