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A subordinate from work called me on my drive home today and asked me if he could share his location with me and if I could tell him where it was showing up. Instant alarm bells started going off in my head. I wanted to know why, but he wouldn’t tell me until I reported back on his location. After I answered, he explained that he was still living with his ex-girlfriend for the purpose of sharing rent, while he saves up for somewhere else to live. He started dating a new woman 9 months ago, but told her he was living with his sister instead of his ex. Apparently the ex found out, contacted the current GF, and told her they were living together and still dating "out of jealousy."

He continued to lie to CGF and deny it, and he was on his way to his sister’s house to pick her up, bring her back to his place, and take photos with her there to send to CGF, and he didn’t want her to see his location moving. Of course I told him he needs to fess up, that you can’t start a relationship on a lie, of course she’s going to find out eventually, and then it’s going to be even worse because they will be more involved and he will have told more and more lies. I suggested maybe she would understand why he didn’t want to tell her about his living situation and give him another chance if he confessed of his own accord and promised honesty going forward. He replied, "No, then she’ll definitely break up with me!" And I told him it’s her right to know the truth so she can make that informed decision for herself. Of course, he didn’t want to listen and wouldn’t be convinced, and we hung up as he arrived at his sister’s.

I’m angry with him for making me complicit in his scheme, and for lying in general. It’s especially bad that he’s telling me this, as I’m responsible for grading his performance at work, and now I have to worry if I’m being objective or not. I will most definitely be on the lookout for any work-related dishonesty, that’s for sure.

What is the probability that he is/was still involved with the "ex" and two-timing both women? And do I have an obligation to try to seek one or both of them out and inform them? I don’t know how I would even go about doing that, or whether it’s prudent.

Help!

That is a moral quandary! I would be torn if I was in your shoes, too.

Do you have a HR person you can talk to about this? I would probably start there to check on any possible legal issues or workplace policies that would impact your decision. If you're worried about staying objective, you might want to ask that this guy be transferred to another group. That would also give you more leeway in reaching out to his ex or CGF.

He replied, "No, then she’ll definitely break up with me!"

The probability is over 100%.
I bet he cheated with her on his 'Ex gf' and very likely he is cheating on her with his ex gf, otherwise there will be no such fear.

He is a liar and a cheater (careful for the loyalty of such person at work)

And I told him it’s her right to know the truth so she can make that informed decision for herself.

And you told the only good moral and sensitive choice.
You did well

Key word is subordinate.
As a manager you can be friends with your subordinate, but there needs to be a relatively clear cut-off point.
If he’s calling you off work hours and asking you a favor as a friend... then there has to be that friendship in place. However based on how you write about this scenario then it sounds more like a friendly work-relationship, and not a "friendship".
Like... if this guy changed jobs tomorrow, would he still call you or would the two of you go watch a game together?

My take – as a manager with subordinates...
I would take him aside AT WORK and give him a verbal informal warning/reminder about boundaries. I would do it in a way where I would point out that by involving me in a non-work related issue outside of work he was placing me in a predicament that could possibly impact my career and/or the company. I would make it clear that if he thought personal issues were impacting his work performance you would listen and try to resolve with him, but that THIS particular instance was outside of work-hours or normal expectations of work-based relationships.
I would make it clear that this is an informal talk, with no future impact.
I would also probably offer him some advice: Simplify life, and the best way to do that is to live by honesty.

In his instance, the honesty could be that he and his ex GF could be honest about the BF/GF being over, or being honest to himself that the present living situation isn’t realistic, or it could be in being honest to the woman he’s dating.

But... after that... I would simply leave him to his own issues – cheating or not. After all – there core issue you are complaining about is the unclear line between work and personal life.

The nature of the work we do tends to encourage bonding outside of what is considered "professional." Most of us are fairly close with those at or near the same level of seniority and will spend time together outside of work hours, given the opportunity. I’m not sure why he didn’t go to his peers with this whole situation. It could be because last year I noticed he seemed really down, and when I asked him what was wrong, he said he was going through a breakup, and I tried to offer him some comfort and advice. Maybe he felt that this is a similar ballpark. It probably would be best to create some new boundaries.

The company would be more inclined to send me elsewhere than him, and having experienced working elsewhere, I would really, really prefer to stay where I am. This particular dude was supposed to be promoted to the same level as me a while ago, but he’s missing some necessary training the company has neglected to send him to. Now he’s stuck in a loop of "you need to do this before you can do that, but also you need to do that before you can do this." I was assisting him with getting that corrected, but now I’m not sure I should. If he does promote, I’ll still have seniority, but I won’t be in charge of grading his performance any longer. But then we’ll have a dishonest person in a position of authority over others.

What if I stop assisting him, do my best to remain objective about his work, keep an eye on him, and let the dice fall where they may with his promotion, while trying to create a more professional boundary here? And maybe the women will figure out what’s going on by themselves, since they’re already in contact?

Regarding the idea that you would have a "dishonest" person at your level of leadership?

You yourself cheated. Your current wife cheated.

The fact is that you do not even know if others cheated, those below, equal to, or above you.

The president of the USA cheated multiple times. The Secretary of Defense cheated multiple times.

If we eliminated all cheaters from having any chance of promotion at work….