For This Relationship, It's Judgment Day

Dear Sugar Radio is a weekly podcast from member station WBUR. Hosts Steve Almond and Cheryl Strayed offer "radical empathy" and advice on everything from relationships and parenthood to dealing with drug problems or anxiety.

Today the hosts are presented with a question that requires thinking about honesty, trust and judgment in relationships. A woman writes that the man she's seeing recently confessed to having cheated in past relationships. She's concerned — not that he'll cheat again, but that he hasn't expressed much regret for doing it in the past. Is she being too judgmental?

Dear Sugars,

I recently met a great guy I'll call "Richard" on a dating app, and we've been seeing each other pretty regularly for about a month. Recently, he shared with me that he would like our relationship to become exclusive and for us to be boyfriend and girlfriend. I've been single for about four years (I'm 30), and I would very much like to be in a committed relationship. I told him that I wanted the same thing, but that I'm still in the process of getting to know and understand him and I needed more time.

Since then, we've shared details about our past relationships with each other. He revealed to me that he cheated on every girlfriend he ever had when he was in college and in law school. He says he has not acted this way for about seven years, and he has since had other girlfriends to whom he was faithful.

When he told me this, I tried to remain open and non-judgmental. I asked him how he was able to rationalize this behavior to himself, and he said, "To be honest, I just turned that part of my brain off." He emphasized that he was much younger then and he was "sowing his wild oats," and that he wouldn't cheat on me now because that simply isn't what he wants. He wants someone to spend time with and be in a committed relationship with.

He is a very matter-of-fact type and doesn't mince words, so I take him at his word that he doesn't have any plans to resume his cheating ways. However, there are a couple things that concern me about this.

One is that he didn't express much regret or self-reflection. It seemed as though he was saying his bad behavior suited his desires back then, but they don't now, so he has cut them out. But what I want is a man who has values and principles that guide him through life — not someone who picks and chooses when doing the right thing suits him.

The second thing is that some of his friends continue to cheat on their girlfriends or spouses. While he acknowledges that their behavior is scummy, it's odd to me that he can be friends with people like that. I know this might sound super self-righteous, but I can honestly say that the people I surround myself with are good people who do not cheat on their significant others.

Am I judging him too harshly for cheating all those years back? Should I be giving him credit for being forthcoming about it? Or is it obvious that he doesn't have a strong moral compass? I so would like for this relationship to work, but I'm not willing to commit to someone I don't deem trustworthy. Sugars, what should I do?

Signed,

Too Judgy, Or Not Judgy Enough?

Steve Almond: TJONJE, it sounds like what's unsettling you is that this guy doesn't have an adequate capacity to self-reflect and tell you, "Not only did I do these things, but I know they're wrong because they were hurtful to the people I was with."

You believe his declaration, but there's something untrustworthy about how he's saying it. It's like when you say to somebody, "I'm sorry that upset you," as opposed to, "I'm sorry I said something that was clearly hurtful to you." It feels like he disassociates a little bit. I think you need to have a talk about this before it goes any further and say, "I know we talked about this and I know you think the issue's over, but it's not for me."

Cheryl Strayed: I think you're being too judgy, TJONJE. I don't mean to say that you don't have some valid concerns. It seems to me that the most important concern is Richard's sense of regret. I would want to know if he has really thought about the consequences of his actions. But I think that's implicit in the fact that he told you about these things, and that he spent the past seven years not cheating on girlfriends.

You ask if he's trustworthy, but maybe you should ask: What does trustworthy mean to you? Does it mean never having made a mistake? Or does it mean telling you the truth about his life?

If it's the latter, you've got that. This man has admitted his past mistakes, even though he knows you feel judgmental about them. Would you rather that he doesn't tell you those things?

I'm not saying it's OK to deceive and lie and cheat. But I am saying that a lot of people make mistakes within this realm of life, and it doesn't necessarily mean they're immoral. The guy I would be much more afraid of is the guy you met on the dating app at the age of 30 who claims to have an absolutely pure background. Lower those judgments. Open your mind and heart. Have some real discussions, and make yourself vulnerable.

You can get more advice from the Sugars each week on Dear Sugar Radio from WBUR. Listen to the full episode to hear more from people doubting their relationships.

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