Ask Wendy

How Do I Cultivate Love When I Have a History of Sabotaging My Relationships?

Friday, May 31, 2019
Hey Wendy,

I loved your dating workshop! Thank you for saving me a lot of time and trouble. I am finally ready.

I set up an online profile and I’m getting plenty of responses even though I’m 59 and a single mom with a five-year-old boy. I am awesome!

I’ve been corresponding with a man’s man. Thanks to you, I recognized that I couldn’t keep him at a distance any longer and I’ve connected with him by phone. I’m excited and terrified to get to know him.

Here’s the problem…Five years ago, I emerged from a twelve-year, deeply lonely, waiting-to-die marriage. I’m angling things towards failure, and that’s not what I really want. How do I upend a lifetime of sabotaging men who actively support me?

Pamela — San Diego, CA

Hi Pamela,

I’m glad to hear you’re out there and moving toward what you want in life.

The men you attract are not your ex-husband, so you don’t need to worry about sabotaging them out the gate if you’re willing to see them as new and shiny instead of as new manifestations of past pain. If you can do that, you’ve solved part of the problem already.

And men are responding to you! Have you ever heard the phrase, “And wherever you go, there you are”?

Honestly, your question, “How do I upend a lifetime of sabotaging men who actively support me?” just might be above my paygrade. If you need to break a lifetime habit, I recommend you invest in a good therapist who can not only help you identify the root of the trouble but also guide you in creating new habits that will cultivate happy, healthy connections (a moment of navel-gazing never hurt anyone). That’s one path that can help you move forward in a new, different and positive way.

When you’re in “good working order” and you’re already ready to date and create a new partnership, trust that you have learned from your past and be willing to be vulnerable and open to a new person—while smart enough to wait and see what you can trust this new person for.

To avoid another deeply lonely relationship going forward, express what you hope for in your partnership with your new person when the timing is right, and pay attention to their receptivity and willingness to be on board with those desires. Fill your life with friends, family, and colleagues to share your time, energy, gifts, stories, and talents. It’s hard to be lonely when you’ve surrounded yourself with a solid community (or a set of communities) and you’ve balanced self-care with focusing on others.

Good luck out there, and I’m glad my dating class helped.

Do you have a dating, sex or relationship question for Wendy? Send it to Wendy@WendySpeaks.com.