4 awkward love life questions – and some smart answers


A date will often be curious about your conduct in the past, as it could give indications as to how we would be in a relationship with them. They may try and establish this by asking some awkward questions 

1. “How many relationships have you had?”

This can be a very awkward question particularly for people who have had a string of bad relationships but also for people who have had very few or maybe not been in a relationship for a long time. Having lots might give the impression that you have issues with commitment while too few could indicate a lack of experience. Either way your experience is your experience and it can be comforting to think of you previous relationships as stepping stones taking you to the one that is right for you.

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As with any personal questions it is not advisable to go into too much detail on the first few dates. Wait until you are in an established exclusive couple before you really open up about matters of the heart especially to do with exes.

Smart answer: Enough to know what I want now.

2. Why did your last relationship end?

This question can come up quite early on in dating conversation – it is natural to want to know how come this gorgeous creature in front of you is on the singles scene. The key to answering it is to keep it brief and to not use it as an opportunity to offload all your hurt and resentment about your ex – no matter how justified your feelings are no date really wants to know all the ins and outs of a bad break-up – or even a good one.

They are asking to find out that it is really over and that you are emotionally available for them. In order for this to be the case you need to have come to terms with the past and not be carrying it around with you.

Smart answer: Because if it hadn’t I wouldn’t be here with you.

3. Do you believe in monogamy?

Any question to do with sex can be awkward when you are first dating. It is a sensitive subject and one that is likely to come up if the person you are dating has been cheated on in the past. They are asking because they want reassurance that they are not going to get stung in the same way again. It can be a particularly awkward question if in the past you have been unfaithful to a partner or been promiscuous but again the key is to avoid over sharing. Answer truthfully from where you are today rather than going into details about how you behaved in the past. If a monogamous relationship is not what you are looking for it is best to be upfront about that from the beginning.

Smart answer: Today I know what is important to me.

4. When did you lose your virginity?

This can be an awkward question because people are afraid of being judged by their answer. If a date is asking this – or any personal question – and you don’t feel comfortable talking about it then it is fine to say that. If you do answer keep it brief, factual and light – many people have funny anecdotes 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.

Smart answer:  Does it count if I found it again?

These are just a few examples of awkward questions that might come up of course there will be others. With them all remember the 3 golden rules when anyone asks you an awkward question:

 – Smile to relax the atmosphere between you and the question poser. If you are embarrassed about the answer, smiling or laughing can release your tension.

 – You don’t have to answer every question someone asks; it is ok to say ‘I’d prefer not to answer that.’ As you get to know them better you might choose to reveal more.

– Don’t over share in your response – remember your date is trying to establish whether youc   are someone they want to pursue a relationship with – they don’t need your whole life story to do that.

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