Regrets in love will hurt more

Miami was awesome. I landed back in NYC on Monday and was greeted by a sunny city!  I love the warm weather (hence why I take as many beach vacations as possible), so coming back to a city that was warm was awesome.

Enough about the weather! You want your love note for this week, right?

This week I was thinking about my clients and found myself noticing an interesting thing that happens when clients first sign up with me. Without fail, relationships that had little closure in the past seem to start up again because these men come back and start to show interest. Continuously someone will sign up with me and that week they will tell me they received a text message from a guy they dated several months ago, hadn’t heard a peep out of, but was someone they really liked and didn’t know what had happened!

This week it was Mary. Mary had a guy she had dated for 2 ½ months. He was super attractive and took her on epic dates, like the time they went to a screening of Casablanca on a rooftop. Isn’t that crazy romantic??! Overall, he made her feel special when they were together. Now the catch here was that he would emotionally withdraw often (not calling for days at a time) and there had been a lot of miscommunication between the two of them. Eventually they stopped dating because Mary was having so much anxiety during the times he would withdraw, that she would be gun shy to express herself because she feared she was doing something to cause him to withdrawal. At that time he also wasn’t emotionally ready to really let her in.

Mary signed up with me literally a week ago and Jay emailed her this after months of no communication:

“Hi Mary,

I would like to see you. I owe you an explanation about what happened between us and what’s different now for me. Do you have any free time this weekend?

I hope you’re having a great week.


ps I know it’s a late but please don’t be concerned that I’m out late and
writing a drunk email. I am not. I just happen to be up late.”

So, what did Mary do? She met up with him, and HE confessed that he had made a huge mistake, that he would really like to keep dating and that he really believes that there is something serious in the future for them. Now, Mary was blown away by this. She didn’t even quite know how to take it all in. She was confused, excited, and scared to try something with someone that had hurt her so much.

Therefore we got Mary clear. First we had to shift through all the fears such as:

  • What if he disappears again?
  • What if I am wasting more time with him when I could be dating others?
  • What if I am not able to break it off even when it isn’t working?
  • What if he doesn’t communicate the way I need again?

Then, the big question: If none of those fears were valid because Mary had all the time in the world, wouldn’t be hurt if it didn’t work out, and could be on the same page communication-wise, would she want to be with him? She emphatically said YES.

The only answer for her then was to try it out! Her initial response was that she was fearful that she may be hurt again if it didn’t work out. She was already projecting that it would end to save herself from pain and from dealing with the fear. This is so normal.

I explained to her that no one ever knows if it is going to last. I am married and I don’t even know! I absolutely hope it will, but there are never any guarantees.

Love isn’t about locking down an answer about if someone is going to be with you forever; it is about having no regrets. 

I am telling you about Mary because so many of you are allowing your fears to override what you desire in your dating life, and you have many regrets because of that. You have a choice! You always have a choice! Allow the desire of what you want absent of the fears to help guide you in your decisions. A question you can ask yourself is, “Would I regret not trying this out?” If the answer is YES, then honor that.

Your Lovework this week:

Ask yourself how fear is getting in the way of having the love you desire in your life right now. What do you truly desire? Are you making choices that allow you to have little regrets?


In Love,


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