This Digital Series Explores The Intimate Weirdness of An Older Woman/Younger Man Relationship

In Conversations In L.A., a 40-something contemplates marriage with her much younger boyfriend.

What happens when a younger man tries to pop the question to his much older girlfriend? She almost causes a traffic jam! That’s one of the issues explored in the second season of Conversations In L.A., a dark comedy that has returned to iTunes and Amazon for season two.

Anne Marie Cummings (who created, wrote, directed and stars in the digital comedy), plays Michelle Macabee, a woman facing menopause and the loss of her pet hamster, and is in a torrid love affair with the much younger Gus, played by Gustavo Velasquez - who’s ready for a meaningful relationship. Michelle has already grappled with the notion of having just a boy toy versus truly being in love. But taking it to the altar level, that’s a whole new season worth of complications.

Anne Marie and Gustavo give a little sneak peek of season two and explain why older woman/younger man relationships are so misunderstood.

It's season two of Conversations in L.A. What twists and turns can we expect? 

Anne: The tagline for the season is “Friends, Family, Therapy,” with an additional tagline “the conversations get deeper.” What you can expect is the unexpected. I take all of the characters on a deeper journey of dealing with their darker truths, the things that weren't discussed in season one, the things people leave out during the honeymoon phase of their relationship. In season two, all masks are off, and when they aren't, they get removed by somebody else. 

Gustavo: In terms of my character, it’s a deeper journey. Gus has to be accountable. He has to take a hard look at himself and make the difficult decision to be honest in his relationship -- if he wants it to lasts. He gets challenged about his past, and so does Michelle. That's what happens in relationships. Two people meet and they have their pasts they have to overcome, in order to move forward. 

Anne, have you been involved with younger men before?

Anne: My relationships with younger men have been awesome and also very challenging. What's so wonderful about the older women/younger man relationship is that young men can be vibrant and funny and sexy and mature, all wrapped in one, and that's very refreshing for an older woman if she has her s**t together. It can be a relationship where two people learn from each other, maybe more intensely than when you are with someone your own age, because of the different perspectives. In my experience, neither person is necessarily the wiser. Hopefully, you will follow your heart because it hurts when you don't. 

And Gustavo, have you been involved with older women in real life?

Gustavo: In the past, I have only dated women my own age. Although I have never dated an older woman, I would welcome the experience. But, age is not a concern for me. I feel people have not fully realized themselves and should continue to work on themselves instead of looking for what's missing in someone else. I'm on a journey of self-exploration and when I meet someone, I look for an awakening of the mind, spirit and soul. It has nothing to do with age. 

Is the series based on real-life experiences? 

Anne: Not at all, but I am a woman in her forties and I often start with myself as a point of reference as a writer. I like to write about love and make people feel connected to characters who are going through real-life experiences, and they can relate to people are willing to take more risks for love. Here we have two people who need each other, but face obstacles like so many of us do when we are in love. 

What're the biggest misconceptions people have about older women dating younger men? 

Anne: That it's just about sex, which is so overrated. Relationships are so much more than sex and physical intimacy – they are about the way two people’s minds connect, how two people stimulate each other intimately. The older women younger man relationship is no different.
Gustavo: Again, most people have not fully realized themselves. Regardless of age, they look for quick relationships to fulfill the emptiness they feel. It's easy to go out to bars and look for someone, and it's easy to go on dating apps and meet someone physically attractive. It's even easier to fool yourself into thinking that the other person wants more than just sex. It's extremely difficult to find happiness within yourself. When you find a deep connection, it has nothing to do with age or sex. It's just real. 

What advice would you share with women and men who find themselves in an older woman/younger man relationship? 

Anne: I've had enough experience in my life to know that when love comes, it just comes and, you can fight it or you can go with it. So as different as it may seem for an older woman to be with a younger man. If there is love, you can make it work. You have to be open. Be patient. Understanding. Willing to talk. Truthful. See if the two of you can push each other to be the best people you want to be. See if there is a future with that person. Bottom line, it's worth giving it a try. All love is worth trying. 

Gustavo: Go through it. Have the trial and errors. Only through bad experiences can you ultimately learn the lessons you need to find what really works. And, what really works is finding yourself. The divorce rate is through the roof, most married couples either cheat or are unhappy. They pretend they are happy in order to fit in society's status quo. It's ok to not be married by 30, or 40 or to never get married. It’s better to be alone than with someone who does not see you for who you really are.  

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