Too Many Red Flags



Dear Dharma,

I am a single professional woman, 38 years old.  I am relatively successful, have a solid, stable career, and am paying off a condo in a nice part of the city.

I have had a 5 year off again on again relationship with a guy 2 years older than me.  It is currently off, and maybe for the last time.

We have always had different views on money.  I am a saver, he is a spender, and I have on a couple of occasions lent him small amounts to cover emergency bills (once for his car, and once for not covered medical costs).  He has eventually paid me back, but it was enough to make me leery.  After the last breakup I felt like he was never going to be any different and I was kidding myself to think otherwise.

Now he is contacting me again, saying he wants to get back together, and that we should seriously think about moving in together.  My place is big enough for two, and whenever we stayed together in the past it was always at my place, so I know it is workable. He says if we were together full time, we wouldn’t have money arguments anymore, and everything would be great.

Part of me says no way, but we do have a history, and when things are going well, we have a great time.  Am I being too harsh on him, and should I say ok, let’s move in together, or should I listen to that little voice that says I will regret it?

Not the Sugar Momma

Dear Sugar Momma,

I don’t know why we conversationally refer to that “little voice” inside of us as little.

We should relabel it to something more accurate, like “the thunder within”, or “the thing I should never, ever ignore”.  I think I’m going to submit an application somewhere to get that changed, but in the meantime, we should certainly never condescend to our intuition by calling it little.

My dear friend, the red flags in your letter are many.

First off, Dharma twitches to the status of “on again, off again.”  Except for Rachel and Ross (who may not even be together anymore for all we know, since they refuse to do the reunion), this never works in the long run.  The “off again” portion of that equation almost always wins.

Secondly – and let me get this right… him moving in with you is “workable” because your place is… big enough?

And wait, the money arguments would magically stop because… ummm… because he said they would?

You’ve already put 5 years into this relationship, and that “history” is what’s holding you captive.  Do you want that to turn into 10 years, 15 years?  Do you want to be in your mid 40’s saying to me, “I don’t know what to do, Dharma!  My relationship sucks, but gosh, now there’s even more history to bind me!”

Be smart, hold firm on the “off again” – and trust your gut.  It’s one of the biggest assets you possess, and you need to treat it respectfully and accordingly.



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  • Irene says:

    Yikes!! Steer Clear SUGAR MOMMA!!! Your intuition is your strongest tool! And you’re only 38 years old. You have a long life ahead without heading into the role of being a purse and one day a nurse!

  • Susan says:

    Yes, listen to your instincts. I wish I had. I paid dearly in almost every way you can think of. I will be selling my dream home and filing for divorce but I know I will be happier, able to pay all my bills and still be able to travel the world. Good luck to you❤️

  • Ellie says:

    Definitely stay clear & don’t let a little sweet talk get you back to where you were before. 5 years is better than 10 years! Money always breaks up relationships and you’ve had more than enough “little flags” to tell you to ‘Run, Sugar Momma!, Run’!! Good luck!

    • Dharma says:

      Totally agree, Ellie – 5 years wasted is bad enough, no need to throw more time at this situation to know what’s the best thing to do!

      Thanks for your comment!

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