Wayne and Wanda: I asked my new boyfriend about previous relationships. Now I don’t know if I can trust him.

relationship stock

Dear Wayne and Wanda,

I’ve been with my boyfriend for a few months exclusively. Before that, there was a period when we were dating but not serious. I really like him and could see a long future together but a recent red flag has me worried.

We finally had the “past relationships” episode. We hadn’t really talked about it before. My history is pretty boring. A couple of long-ish relationships. I’ve never lived with a partner.

He was in what I’d consider a long relationship — three years. Then he shared they broke up because he cheated. Maybe I shouldn’t have asked for details but I did. He cheated on her more than once with more than one person during most of their relationship.

This had me freaked out that I entered a relationship with someone who wasn’t capable of fidelity. So I made maybe my second mistake and asked about those few months when we were getting to know each other: did he sleep with other people then? He said yes, he did — but we weren’t together officially, he said, and he insisted he’s matured a lot and he’s all in on our relationship.

I don’t know if I can trust him and our relationship knowing all these new things I didn’t know before. Any advice on how to get past this or should I listen to my intuition and cut him loose?

Wanda says:


At a certain age and level of experience, we all have baggage when it comes to our romantic lives. This begs the question, when you enter a new relationship with a new partner, how much do you want and need to know?

Curiosity is human nature, and when we’ve found someone we’re newly interested in, it’s at an all-time high. Some information about a partner’s romantic past can be helpful. For example, what have they learned that they need to be happy? How do they communicate? How do they express love? These conversations offer tangible takeaways that can strengthen your connection and foundation.

Do we want to know if they treated someone horribly and selfishly? That they were tragically ghosted and embarrassed and hurt? That they spent two years using Tinder on every vacation? You can ask these questions, but you may not like and will likely not be able to forget the answers, and you’re judging the person in front of you now against actions in their past. Is that fair?

It seems like you really like this guy. You weathered the unpredictable open phase while you casually dated, then matured into a monogamous relationship. Will it work out? No one ever knows for sure, and relationships are always a leap of faith, in a way. But you have to have some faith to give it a chance. So give him the benefit of the doubt, remain open-minded, and begin your relationship from a place of trust.

Wayne says:

So, your boyfriend’s honesty about his dishonest activities in a past relationship, and his admission to playing the field while also focusing on you, has you questioning his long-term trustworthiness? Yeah, I see the big red flag, too.

I guess we’ve got to give him some credit for being an open book and telling you some hard truths. But dang, it’s almost like he’s proud of it. And that’s honesty to the point of self-incrimination to a rap sheet of relationship crimes. We aren’t talking about one screw-up or a few harmless misdemeanors of the heart that you can easily expunge. Sure, adults can and should be able to forgive and forget partners to a certain extent, but he’s testing you right out of the gate!

He strikes me as one of those folks who operate in the gray areas of life. Can’t turn down a thrill, an opportunity to work the charm, the chance to ride the razor’s edge of right and wrong, naughty and nice. Once his relationships and routines turn blah, I can see him dipping his toes into some murky waters, catching a buzz of excitement, and quickly getting himself deeper into trouble.

He told you who he was and who he is — you should listen to him and your intuition. He has the potential to break your heart in a really bad way and live to tell the tale to his next potential girlfriend.

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at