Revealing the intimate details of past relationships is a personal and often sensitive decision. It’s your companion's choice whether to discuss these relationships—he’s not required to explain his past. Evaluate your intentions before asking. You should be motivated to gain insight into your partner's character—to learn what drives him, what gives him joy or what pains him. Addressing the issues from his past may help you work together to create or improve a more understanding relationship.

Wait until you’re in a committed relationship before asking about his past. Allow your relationship to mature before you question him. You should both feel secure in the relationship. Allison Conner, a psychologist and founder of Cognitive Therapy Associates in New York City, agrees that it’s healthy to discuss past relationships to an extent, but they “…shouldn't be discussed in detail during the initial phase of a relationship,” she says in an article on the "Psychology Today" website.

Show a willingness to discuss your past relationships, too. Don’t expect him to open up to you if you’re reluctant to reciprocate. Successful relationships require mutual communication, says social scientist and educator Michael Formica in an article on the "Psychology Today" website. By sharing your experiences, you may put him at ease about the situation, and you may discover that you can relate to each other through the pain you’ve endured.

Be sensitive about the manner in which you initiate the discussion. Unveiling the past can be a painful experience for people. Show some compassion when you address the issue. By opening up to you, he’s making himself vulnerable to the possibility of conflict, rejection or hurt. Vulnerability can benefit the intensity of a relationship, but it must be mutual, says therapist Jef Gazley on Ask the Internet Therapist.

Refrain from using his past against him. Recognize that he can’t change the past, so keep it out of your relationship, says psychotherapist Kristina Randle on the PsychCentral website. Once you’ve discussed it, let it go. Focus on who is he now and why he is with you. He’s chosen to be with you now; don’t introduce jealousy into your present relationship concerning something in the past over which he has no control.

Focus on the positive aspects of the past that have led to your relationship. The past can help people learn from mistakes and teach them ways to improve their lives, so try to see the good that has come from his failed relationships. Grow together as you learn to accept each other in spite of your individual faults, and direct your attention to the admirable qualities that you observe in each another, Gazley recommends.