Redemption For a Douchebag?

May 12, 2016

Bessie writes:

Dear Susan,

I’ve been in a relationship with Jacob for two months, and he’s always treated me very well. However, I recently discovered that he has treated other girls in the past like a “douchebag” would (including leading them on and using them for sex).

I don’t doubt that he loves me and cares about me, he shows it everyday. However, I’m a bit heartbroken to find out about his past, and feel that his past behavior speaks about his character, and possibly also about his future behavior with me. Should I take this as a red flag and move on?

There’s no question that this is a red flag – the question is whether this is a dealbreaker. Can a douchebag be redeemed?

I asked Bessie for a few more details to get a better understanding of the situation. In particular I wondered how she had learned about his past behavior and whether the source is reliable. It is:

We are both 22 years old, and we are both seniors in college, about to graduate. We started dating in late January, although we had met during the summer last year.

Last weekend, he had logged into his Facebook from my phone and he was still logged in when he left. Then, curiosity killed the cat, and I went through his messages and his Activity Log. I saw conversations he had had with girls from before we were dating (some were from a few weeks before we started dating), which is how I learned about it.

He had actually already talked to me about his past, about how he had been closed off emotionally and had probably not behaved well with some girls. He said that the first time he managed to open up emotionally was after he got to know me better. This is his first relationship, and he says he has never felt this way before.
I don’t know why I didn’t make a big deal out of it back then – maybe I didn’t think the relationship was going to be as serious as it is now, or maybe I just assumed that’s how guys usually behave. However, there was something about reading through these messages that made his behavior so much more real, and it made me feel disgusted. I know how it feels to be used.
This is his (and my) first relationship. He wants to change his post-graduation plans to be closer to me after we graduate, but he’s already planning on visiting me weekly or biweekly wherever he ends up. He treats me really well and does a lot for me – he has even made comments that hinted at the idea of marrying me sometime next year. I know it’s early in the relationship, and I know that it’s human that his feelings may change, but right now I don’t doubt he loves me (he has already said it, and says it everyday). However, I feel a bit repulsed at what I’ve found on his Facebook. 
First, let me get rid of the nagging issue that might derail the conversation among readers in the Comments. Yes, she read his private Facebook. I probably would have too. She didn’t go snooping for it or steal his password, he left it sitting open on her phone. I’m glad she read it because she learned something extremely important about Jacob that she needs in order to make a decision about a future with him.

So let’s not focus on Jacob’s right to privacy. Let’s focus on his actual behavior.

On the positive side, it’s only fair to give Jacob credit for having been honest with Bessie about his past behavior towards other girls. It was on his mind, and it probably wasn’t easy to confess bad behavior to a girl he is clearly head over heels in love with. (No doubt that revelation was in the back of her mind when she saw an opportunity to learn more and took it.)

He treats her well – she feels loved and does not doubt his commitment. He’s actively planning a future with her.

He is not secretive with Bessie – checking FB on her phone and leaving it open makes that obvious. I do not suspect that he is being dishonest or hiding anything at the present time.

In short, Jacob’s declared feelings for Bessie are supported by his actions, which is why she feels emotionally secure in the relationship.

But I do see some problems here. We don’t know the specific tactics that Jacob used to manipulate women into having sex with him. But we do know he did this right up to just before he committed to being in a relationship with her. If he knows now that he was being a dick three months ago, he knew it then and he did it anyway. This does reveal a willingness to manipulate others for his personal gain. Maybe he won’t ever cheat on Bessie, but he’s demonstrated a lack of respect for the feelings of others – and that’s an understatement.

On the other hand, between a third and half of subjects in one survey of 1,000 men admitted they would lie to a woman about their feelings in order to get sex:

On Faking Interest to Get Sex

56% of guys in bars said they would fake interest in a girl to get sex
41% of guys not in bars said the same
44% of guys in bars said they would lie about wanting a relationship to get sex
33% of guys not in bars said the same.

Those are big numbers, and they no doubt include guys who will ultimately make good husbands and fathers. Jacob’s behavior most likely reflects the opportunities he faced as an attractive guy in college. That doesn’t excuse him, but let’s remember we’re judging an adolescent who has been mired in hookup culture and the peer pressure that accompanies it.

If Bessie had written to me that she is attracted to a guy with this history I would say his douchebag behavior should be a dealbreaker. There are too many good guys out there to waste time on a cocky asshole, narcissist and/or sociopath. But what if Jacob really has changed? What if falling in love for the first time with a highly ethical woman has inspired him to change his life permanently? Even St. Augustine took a while to come around.


This is a tough call, but I recommend that Bessie stay in the relationship and continue to evaluate his behavior towards her. She’s in love and Jacob won’t be the first guy to clean up his act when he found the right person.

But Bessie needs to fess up to what she read and talk about this more fully with him. She describes herself as being brokenhearted and repulsed by this – it’s clearly weighing heavily on her. The issue will only loom larger if she doesn’t resolve it by expressing her disappointment and giving him the opportunity to respond. Bessie should make it clear that she has concerns about his character, and worries that he might become selfish and dishonest with her in the future.

Jacob’s response will say a lot about his character. Will he take full responsibility or offer excuses? Will he describe more fully what’s different about him now? Bessie should be on high alert in the coming weeks and months to verify his trustworthiness. It’s also possible her own feelings have changed, and she should check in with herself periodically about that too.

Sometimes people do change. The jury’s still out on this one, and Jacob will need to demonstrate over time that he is worthy of her. I will add that if Bessie were to learn that there’s more evidence of selfish behavior and a bad reputation, she should reassess. There’s immature knucklehead bad and there’s sociopath bad. It’s up to Jacob to convince her he’s only guilty of the former.