Hobie & Monk: Dating advice is tricky business

Hobie & Monk: Dating advice is tricky business
(Cat VanVliet)

Dear Hobie & Monk,

My best friend keeps dating — and getting dumped by — the wrong women. First he went out with this girl who complained and bossed him around all the time. He was miserable but tried everything to make it work, and then she dumped him. Then, he started dating someone with the complete opposite personality she was a doormat. He was miserable but tried to make it work, and then she dumped him. How can I help this guy avoid making the same dating mistakes over and over again?

– Best Mate 
to Miserable Dater

Hobie: I’m dying to know if your friend agrees with your assessment of the situation. If yes, then it might be time for him to figure out why he’s willing to be miserable rather than exit relationships that aren’t respectful and rewarding in a timelier manner. Most of us have dated people who weren’t perfect for us — or sometimes even vaguely healthy for us — but after a few bad breakups, we’re often eager for a little postmortem discussion with close friends.

Alone or with you as a confidante, he’ll need to sort this one out to improve his chances of seeking and staying with someone more compatible.

On the other hand, if this is just your opinion, consider the possibility that your friend saw something different than you did in these relationships. Make sure that your concern is solely for his well-being if you decide to ask him for his take on all of this; I’m hoping that you’re not holding out on us by secretly adoring him yourself or holding all of his dates to ridiculously impossible standards for other reasons. And then do what best friends do — listen and know when to keep your advice to yourself.

Monk: It’s hard to watch someone you care about make choices that you feel aren’t good for him, especially when those choices result in misery. I hope you and your friend are able to speak openly about your concerns and his motivations so that you both may gain a better understanding of his rocky dating history. If you don’t see eye-to-eye — or even if you do and your friend sets his sights on yet another doomed prospect — remember these choices are his to make. Then stand by for the next postmortem.

To submit questions 
to Hobie & Monk, email 

Hobie and Monk are two Alexandria women with husbands, children, dogs, jobs, mortgages, unmet New Year’s resolutions, obsessions with impractical shoes, English novels … and Ph.D.s in clinical psychology. Their advice, while fabulous, should not be construed as therapeutic within a doctor-patient context or substituted for the advice of readers’ personal advisors.