Follow Up – Dating and Debt Disaster Part 2

by TTMK on October 11, 2012 · 2 comments

Money and dating doesn’t have to be complicated, but sometimes circumstances make it so.  Or, perhaps better put, people’s reactions to circumstances make things complicated.

Here we will continue the story from the previous post, which discussed a relationship where dating someone in debt was the issue, and a guy I know got burned by it.  Specifically, he helped pay his girlfriends’s debt, only to have the relationship end. This caused him great frustration and an apparent feeling of being ripped off, as he kindly gave money only to see it disappear.

Well, if you read that post, you might have caught the very end of the post where I noted that the woman wanted to make up with him.  How do you think that went?

What happened was he was – for some reason he can probably best explain – anxious to get back together with her.  Now, he even took the noble approach of really doing self-examination on why she might have ended things in the first place.  Without getting into details, I can’t see how he could blame himself here in any way, but again I give him credit for being overly tough on himself.  Bottom line is that he was hoping things would get straightened out.

Only thing is, after a while, the topic of money came up once again.  She made it clear that she didn’t want him to bring up the prior money issue, and just to leave it alone that he paid for her debt.  Further, she said that she didn’t want a relationship where she felt like she was being expected to help him out financially.  This meant paying him back for his help on her debt, or in terms of being expected to contribute much to paying for him on dating.

He told me all this, and was talking himself into thinking that this made sense.

I’m usually one to just listen and be supportive, but in this case I asked him why he felt that it was okay for her to do that? She was just as capable of working and sharing expenses as him, and there was no reason for him to be paying for her all the time and helping with her debt too.  Frankly, I stopped just short of saying that he was being taken for a ride.

So he ended up giving things a shot with her.  I hadn’t talked to him in a few months after that, but we eventually traded texts just asking each other how things are going. His response included a line about he and the woman are no longer in a relationship.  I didn’t pry, just said that we should catch up soon.  We still have to do so.

That being said, I have no doubt that he never got the money back.  Furthermore, I think that the money issue was a huge red flag to begin with.

Question#1 – Do you think that her position on this had merit, or was he being selfish? Personally, I think that the thing to do would have been to not get involved again with someone who flat out expected to be financially rescued. What do you think?

Question #2 – What would you have told him or advised him to do in this case – if anything? My view was that getting involved again was simply going to result in the same issue surfacing.

{ 2 comments… read them below or add one }

Emily @ evolvingPF October 11, 2012 at 10:16 pm

I must say, I applaud the ladyballs on the ex-girlfriend! Those are some serious demands! Really though, I’m glad she was so up-front with her expectations this time around so that he could steer clear. You are right though that it is very touchy to try to give a friend advice, especially in what might become an on-again-off-again relationship.


TTMK October 11, 2012 at 10:27 pm

Emily – Really? I guess it’s usually fascinating for me to get everyone’s opinion on these things. My first thought when I heard that she had the nerve to make such demands was to be repulsed! Well, I too am glad that it was clear enough for him to stay away. He’s a good guy.


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