Choose the right time. Wait until things become a bit serious with someone before discussing your dating history. You do not need to talk about your exes on the first date, and doing so will likely not land you a second. But, if a month or so has passed and you want to progress with them, now could be the right time.

When should you ask your past relationship date?

wait until you feel comfortable enough with him to ask about his ex, or until he asks you. This is always a solid approach. Eventually most guys, if theyre serious about wanting to be in a relationship with you, will get curious.