New book from NYT bestselling author Lewis Howes is now available!

New book from NYT bestselling author Lewis Howes is now available!


Lori Gottlieb

Dating Is Hard: Why Forgiveness Isn't Always The Answer


Why does finding love seem impossible today?

Technology has made our lives easier in SO many ways, but it certainly doesn’t seem to be the case with dating. This is maybe because of some people’s thinking that they have unlimited options because of dating apps, a shift on what a “happy relationship” looks like, or something else entirely. Whatever the reason, finding love today is hard — and the data seems to back this up as well. 

So how do we get back to basics? How can we find our ideal partner and receive the lasting love we’ve been searching for? My guest today has spent her career answering relationship questions like this one, and I’m happy to have her back in the studio for this episode. 

Her name is Lori Gottlieb, and she’s going to share with us what makes finding love today seem impossible, what it takes to truly forgive your partner, how to avoid dating the “wrong” person for you, and so much more! This is such a powerful interview that I wanted to break it up into two parts and really go over two different topics that we discussed.

I know dating can seem overwhelming at times, so that’s why I’m excited to have Lori teach us how we can set ourselves on the right track to find the love we want. So if you’re eager to know more about this, let’s dive in!

Who Is Lori Gottlieb?

Lori Gottlieb is a psychotherapist and New York Times bestselling author of Maybe You Should Talk to Someone, which has sold over a million copies and is currently adapted as a television series for ABC.

In addition to her clinical practice, she is co-host of the popular Dear Therapists podcast produced by Katie Couric. She also writes The Atlantics weekly Dear Therapist advice column. She is a sought-after expert in media such as The Today Show, Good Morning America, CBS This Morning, CNN, and NPR’s Fresh Air, and her recent TED Talk was one of the Top 10 Most-Watched of the Year. 

With all these credentials, she’s one of my absolute go-to people for relationship advice. Her experience and insights are invaluable, so if you’re struggling in your dating life, this is the interview for you!

The Paradox of Modern Day Love

What makes finding love today seem impossible? 

If you’re like me, you might have noticed that many people seem challenged in finding a great partner. Some find it challenging to stay in a healthy and thriving relationship. So, if you’re wondering why it’s so complicated and challenging for men and women or individuals to come together to be in a happy relationship, Lori is here to help you understand.

“I think it’s because no one teaches us how to love and be loved. We only learn about it through what others model to us. The thing is, sometimes we don’t get the best modeling growing up, but we don’t talk about it in the way that we need to. We end up both wanting closeness and fearing it at the exact same time.” – Lori Gottlieb

We want to be close to someone, but we also fear it at the same time. As Lori said, this causes many of us to get tangled up in a “paradox.” It prevents us from being vulnerable to the people we love so we can’t be loved properly.

But what is the thing we fear about love so much?

“The thing we fear is that love is going to wound us. While this may be true, love has the power to heal, too.” – Lori Gottlieb

Now the thing is, hurt is just a part of being in love. While it’s true that some people hurt their partners in an almost intentional manner, it can happen in loving relationships, too. It can be because of a lack of understanding of our partners or because we just don’t know how to deal with specific situations. It can be because we gave our everything and still our significant others cheated on us. 

Lastly, it can also be because we keep on missing that the problem doesn’t rely on either of us, but both of us. After all, love’s a two-way street. Our actions can create ruptures in relationships, but when we work on these issues, together we can get past them and still make it work with our partners.

“How is what I’m about to do or say going to be experienced by the person I love?” @LoriGottlieb1  

Why Forgiveness Isn’t Always the Answer

In the process of repairing these ruptures, we often seek forgiveness from one another. We think that it’s the answer to all of our problems. However, Lori’s long experience as a therapist has shown that’s not always the case.

“Many of us think this idea that if we forgive someone, that we’ll be set free or heal in some way. I don’t think that’s always the case. … For example, as an adult dealing with parents, we can have compassion for them now because we saw what their life was like or what their struggles were. But we don’t necessarily forgive what they took from our childhood or how they treated us when we’re younger.” – Lori Gottlieb

Lori’s statement might be contrary to what we have learned growing up about how important forgiveness is in our relationships. But if it isn’t the answer to our concerns, both individually and while being in relationships, then what is?

“If you truly forgive that person, great. But if you can’t, that doesn’t make you less of a person. It doesn’t make you less evolved because you can have compassion instead.” – Lori Gottlieb

Lori’s take on healing and repairing relationships is interesting, right? Just because everybody’s telling you to forgive someone doesn’t mean you have to do it too. Lori even went far as to say this:

“When you tell yourself that you forgive someone when you actually don’t, that forced forgiveness can be a trap. That can leave you in a stuck position for much longer than you would be. I think that can do more damage than good. … If you can acknowledge that someone hurt you and don’t feel that you actually need to forgive but choose to move forward, that’s a better place to start from.” – Lori Gottlieb

Essentially, Lori means that you should put yourself in the same situation where you got hurt — in her own terms, “stop fetching water from the same dry well.” And while it’s true that forgiveness is wonderful, sometimes it’s not the answer, and instead, it’s just harmful because it keeps you stuck in a cycle of pain. Just as she suggested, it might be better to move forward and make sure you don’t make the same mistake again.

To Date or Not To Date Someone

In the process of choosing to move forward and stop the compulsion to go back to unloving and hurtful relationships, we get to meet new people — people who might be fantastic for us, and people who we might want to date. But what would the signs be that a new person can be a really great match? Lori also has some thoughts about this process.

“It depends who you are. If you’re someone again who grew up with secure attachment, what looks good to you would be like the Goodwill Account. It is when you need to put five deposits into the account for every one withdrawal that you make. Are there five positive interactions for every difficult interaction between the two of you? … Or if you grew up in an insecure attachment where your parents may be inconsistent, such as being like this [one minute] then another [way] the next minute, that relationship might feel normal to you as an adult.” – Lori Gottlieb

Despite these different styles, Lori advises that it’s still a good idea to pursue healthy relationships that make you feel secure. She further recommends some questions you should answer for yourself to know if the relationship is worth pursuing.

“What is the quality of this relationship daily? What does it look like daily?” – Lori Gottlieb

If the daily quality is solid, positive, and inspiring, that could be a healthy match for you. If it falls short, then it might be worth reconsidering if that’s the right relationship for you. 

When it comes to values, Lori also advises asking questions about a potential partners’ character qualities.

“Is this person responsible? Do they do what they say when they say they’re gonna do it? Can I trust them? Can I trust that they’re going to show up for me in the way that they say they will? Are they reliable? Can they be emotionally generous at the moment with me?” – Lori Gottlieb

These are questions that might not be easy for you to ask or answer but are essential. Lori also advises:

“The number one quality that will predict whether somebody is a good partner is flexibility. Can they be flexible instead of being right? That doesn’t mean that they give up their sense of self and agree with everything the other person says. It’s about being open and seeing another point of view.” – Lori Gottlieb

If you can find someone with shared values, you could have a great quality relationship. If they can also be flexible, that’s an added bonus. Just remember to ask yourself these questions to make sure the person you’re dating is right for you!

Why You Should Listen to This Lori Gottlieb Podcast Episode Now…

Guys, once again, I learned so much from this episode of the podcast! Lori Gottlieb is such a fantastic guest, and her relationship advice is always so insightful. I hope this episode taught you a lot about dating and relationships as well.

All of these tips and wisdom are found in Lori’s book, Maybe You Should Talk to Someone. It’s one of the most fantastic books I have ever read! It really opened up my eyes to so many things and has helped me so much in becoming a better person. If you haven’t checked out her work, please do it now! 

Also, if you enjoyed this powerful episode, make sure to tag Lori, @lorigottlieb_author, and me, @lewishowes, with your key takeaways. And don’t forget to check out her work on Twitter or her website. Give us a five-star rating for this episode on Apple Podcasts, too.

Whether you’re currently in a relationship, still searching to find the right partner, or just curious about the topic, I think you’ll find value in today’s discussion. And remember —this is only the first half of this episode, so make sure to check out Part 2.

If you’re ready to get one step closer to finding the love you want in your life, then I encourage you to listen to Episode 1,190 of The School of Greatness!

To Greatness,

Lewis Howes - Signature

“I think it can do more damage than good when you tell yourself you forgive someone when you actually don’t.” @LoriGottlieb1  

Some Questions I Ask:

  • Why is it so hard to find a partner these days?
  • Is there a way to get into a relationship with someone without hurting your partner?
  • How do we get better at understanding our partner?
  • How does someone heal from the fear of joy when you’re in a healthy relationship finally?
  • How does someone know that they’re in a healthy relationship?
  • Why do people stay in unhealthy relationships for so long?

In this episode, you will learn:

  • Why it’s so difficult to find love today.
  • How to better understand your partner.
  • How to break unhealthy cycles from your childhood.
  • The main traits of a narcissist.
  • The common myths around how to truly forgive someone.
  • Plus much more…
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Lori Gottlieb

Transcript of this Episode

Music Credits:


Kaibu by Killercats

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