Here's Why Molly Really F**ked Up On The Season Finale Of 'Insecure'

Here's Why Molly Really F**ked Up On The Season Finale Of 'Insecure'

Certified dating coach Damona Hoffman shares her four-step plan to ditching bad boys for good.

Published September 15, 2017

He was tall, dark and handsome but he had one fatal flaw. He was nice. As I sat there across from him sipping my martini, I had to keep reminding myself that this was a quality that should make him more desirable.

After dating all of LA’s finest actor, producer, musician types, it was clear that my natural attractions were leading me nowhere. That’s why I decided to design a dating plan for myself called Operation Date Nice Guys (aka Operation DNG). However, creating a plan and acting upon it are two different things.

Having lived this, I gritted my teeth until they nearly bled watching the Insecure season finale as Molly made things messy with her nice guy colleague Quentin then ran back into the arms of Dro. No matter how nice he seems, no matter how well you know his mama, he’s married — not a nice guy to date.

These feelings surfaced for me because I was once Molly. My heart and my head led in opposite directions on that fateful night, but this time things were finally going to be different.

You know a nice guy when you see him:

  1. His clothes are well put together because he actually cares about making a good impression on you.
  2. He compliments you, but not in an overtly sexual or demeaning way.
  3. Most importantly, he does what he says he’s going to do — like showing up on time and calling you the next day.

Everything about the way this man’s button-down shirt rested neatly under his black V-neck sweater and paired perfectly with his wool slacks, belt and shoes said he actually gave a damn. It was how he looked for just the right moment to reach for my hand across the table then held it a little too long so I would know he meant business. Mostly, it was the way he kept showing up. Over time, two martinis became a round of pool, dinner, a movie and a weekend getaway. He just kept being there. Now over a decade, two dogs and two kids later, he’s still there.

Since that time, I’ve made it my mission as a dating coach to show women the value of a nice guy. There are amazing men sitting on the sidelines while women are caught up with feeling butterflies and taming the bad boy because it makes them feel powerful.

It all comes down to power. Dating is an exchange of power: from deciding when to reply to his text through the moment you consent to having sex. Yet, the catch with the nice guy is that there’s no power struggle — it’s an even exchange. The passion is a slow burn rather than a wildfire. When you are so used to living in the struggle, you return to that familiar feeling again and again, even if it goes against what you know is best for you in the long run.

Operation Date Nice Guys (aka Operation DNG):

  1. GET CLEAR – The definition of insanity is to do the same thing and expect different results, so you first have to get clear on who you want to meet. For me, I always became attached to emotionally unavailable men who made me feel worthless in a relationship. To me, a “nice guy” was someone who was respectful and thoughtful who would lift me up, not erode my self-esteem.
  2. FIND A NEW POND TO FISH IN – If you go to the same places and talk to the same people, how do you expect to meet someone new? Online dating opened up hundreds of options to me (and this was 13 years ago) – now the possibilities are endless.
  3. BE PROACTIVE – This is the biggest dating challenge that I find with women today. We are so tied to the idea of chivalry that we were sold as kids that we become stuck in a state of inaction. Just waiting for messages to come to you online means you’re missing out on the upper echelon of men. The men who are worth your time aren’t sending form letters to dozens of women. The high-caliber men are impressed by a confident woman who makes the first move. You also have to remember that in the first phase of online dating, you are dealing with computer algorithms, not chivalry. By initiating contact, you are programming the site to feature you more prominently and exponentially increasing your chances of making a match.
  4. TAKE YOUR TIME – We are in such a hurry to determine if someone is a match or not on the first date that many women are overlooking quality men because they didn’t feel that nebulous thing called chemistry. If you really want to know what someone is like, you have to get past the first date.

Molly knows Dro will break her heart in the end but that power struggle is routine for her so she keeps reliving it while dismissing the nice, stable, secure guys who pursue her. Dating men who are unavailable is a dead end street and if you don’t hold the men you date as well as yourself to a higher standard, this situation will play on repeat.

A nice guy makes you feel like you’re the only woman in the world. A nice guy takes care of you in sickness and in health. A nice guy is a full partner in parenting. True power is in knowing when you’re headed down the wrong road and taking action to change course. We’ll have to wait till season three of Insecure to see if Molly’s ready for a nice guy, but are YOU ready to give Operation Date Nice Guys a go?

Written by Damona Hoffman

Damona Hoffman is a certified dating coach and TV personality (from #BlackLove and A Question of Love on FYI TV.) She gives weekly dating and relationship advice on The Dates & Mates radio show and podcast.

(Photo by: Quincy Gow)

(Photos: HBO, Justina Mintz/courtesy of HBO, Quincy Gow)


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