Questions To NEVER Ask An Older Woman 

When it comes to getting to know your date better, the best place to start is by asking questions to find out more about them. This can sound innocent and risk-free enough.  But there are certain questions that you really need to steer clear of when you’re dating an older woman. Questions, which you may have got away with asking in your youth have now become totally inappropriate. For mature single men dating over 50, here’s a quick guide of which questions to never ask an older woman you’re trying to impress.

Questions to Never Ask An Older Woman

Whether it’s date 1, 2 or 5, at all costs avoid voicing any of these questions if you want to see your potential partner again. Period. Oh and don’t mention those either.

Is this an old picture of you?

The thing with online dating is that we all use pictures where we look our best. After all, it’s like looking through a catalogue, our personality can’t beam through by mere glance of a picture. So if you think your date looks a bit older or heavier than the picture on the site, just keep quiet about it. You don’t want to destroy the confidence of your date and you could potentially ruin what could be a great relationship.

Are your children always like this?

If you’re dating an older woman who has children then you need to understand and respect that they will always come first. So if she’s brought them along or you’ve been shown a video, there’s just no need to comment on them in a way that could be seen as negative. Keep your opinion to yourself on this one. 

Why are you single?

That old cliche question that everyone hates to answer. It’s probably harder to answer as you get older, and doesn’t really serve any purpose. You’re both single, so focus your energies on finding out if there’s a connection and you would work well as a couple instead.

My ex wife used to do this…would you try it?

Nobody wants to be compared to an ex. In fact any ex chat is best kept to a minimum in the early days of dating. You’re both looking to move on and start afresh, so there’s little need to be talking about what your previous partner did, and definitely not worth asking them to do the same, whatever it is. You’ll not only come across as rude,  but also insensitive and actually a bit of an idiot.

How many people have you had sex with?

This is never a good question whether you’re 18 or 80. For a start it’s none of your business and secondly it can come across as though you’re going to be judging your date based on the number of partners she’s had. Steer clear of any chat about past relationships, especially on the first couple of dates.

Are you menopausal?