Is it Okay to Keep Dating Someone Still Living With His Ex?

I came upon your site after searching for dating advice while feeling sad at work. I met a guy online and we hit it off really well. On our second date we spent 8 hours together just walking and have seen him consistently 2 or even 3 times a week for about 6 weeks.

The problem is I started wondering why he didn’t invite me to his apartment, which he owns and isn’t far from my place. I asked him about this and it finally came out that he is living with his ex-girlfriend. Basically, she is living there rent free and has been for 10+ months, so she can save enough to move out (we live in NYC). When I asked him when is she moving out, he just said, “maybe the end of the year”, which is still 4 months away. He said that he feels bad for her because he knows what it’s like to be on your own and how scary that is. Plus she was instrumental in him buying the apartment (going to open houses when he could not, etc.) and so he feels like he should help her out.

I saw the apartment – they sleep in separate rooms. However, her stuff is everywhere, as I imagined. Also, he has not told her about me and does not want me there when she is there.

He claims that they do not have feelings for each other and hardly see each other since he works long daytime hours and she works nights.

Should I continue dating him under the circumstances? I really like him. But….eek.

Thanks,
Amy

Once upon a time, I had a client break up with her boyfriend because, among other things, he lent $25,000 to a girlfriend who never paid him back. My client took this as a sign that he had terrible financial judgment. I took it as a sign that he was generous and trusting. Kind of funny how two people can look at the same situation and see completely different things. (By the way, they got back together and are now married with a kid. I love my job.)

Anyway, this feels like one of those situations. You meet a guy who has been nothing but consistent and kind for the past two months. He’s acting like a boyfriend. He owns his own place in NYC. He no longer wants to date his ex, but given her financial circumstances, he feels bad throwing her out on the street.

Who knows, maybe you’ll one day be the beneficiary of this gentleman’s extraordinary patience and generosity.

Again, from where I sit, this sounds like a sweet, generous, sensitive guy. He’s treating his ex the way I would hope you’d treat your best friend. Now I can’t vouch for the ex-girlfriend. I don’t know how motivated she is to move out when she’s living rent-free. But I do know that the question I would have about the guy you’re seeing isn’t about whether he’s up to anything fishy, but simply whether he has the balls to give his ex a deadline for getting her act together and moving out.

I get it: it’s certainly inconvenient — for both you and him — to have her in his space, but, if your relationship is strong, this arrangement won’t last forever. So, Amy, would you rather give him an ultimatum to kick her out in the next 30 days, or continue to enjoy this relationship for the next four months, with him sleeping at your place? The answer seems pretty obvious to me.

And who knows, maybe you’ll one day be the beneficiary of this gentleman’s extraordinary patience and generosity. That should be something for you to think about, instead of stewing in your own juices that this guy is sacrificing for someone he cares about but is no longer dating.