There is a lot to think about when you are dating someone new. There is the excitement of getting to know someone completely different, as well as the nervousness that can sometimes come with potentially starting a new relationship. As well as portraying yourself in a positive and complementary light, you will also want to be upfront and honest. This is why you should tell a new date about the matching tattoos you have with an ex. Regardless of how large or small the tattoos are, or how long ago you and your ex were together, a new date will appreciate the honesty.
The majority of people won't mind that a new partner has a matching tattoo with an ex, as it's something a lot of people have. It's not uncommon to get matching tattoos when you are in a loving and committed relationship, so it's not uncommon for people to have matching tattoos once those relationships have come to an end.
Of course, this doesn't mean blurting out the story behind your matching tattoo on your first date. You wouldn't suddenly delve into when and why you have any other tattoo without being prompted, so it's no different with a tattoo you got with an ex. However, if the conversation heads that way, it's always a good idea to let them know about a matching tattoo. Not only will they appreciate the honesty - think about it, no one wants to hear a story behind a tattoo only to find out something different further down the line - but it gives them an insight into your past relationship.
There is no right or wrong time to tell a new date about a matching tattoo with an ex, but it's certainly not something to gloss over or skirt around for too long. This could be seen as being dishonest or vague, and dating someone new is all about getting to know them and their life. As soon as the conversation comes up, go with the flow and casually mention your matching tattoo. The chances are, your new date won't mind and they are unlikely to give it a second thought.