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Cheering each other on


“I’m 35 and potentially doomed. My baggage is that I love too much too quickly and I love profoundly the wrong men. I see the signals and don’t read them. I don’t know what it is. I have talked my poor mother’s ear off about this. Thank god we can laugh about it! I don’t want to lose hope. But I’m scared that this is my path—that I will constantly love men who don’t love me in the right way. I’m looking for a new perspective, something to keep going so I can keep the faith that I will get married and have the kid that I want.” —Malory

Hi Malory,

Nooooo, you’re not dooooooomed! 🙂

Mostly because your sense of humor will, as you already know, be your savior. That and your self-awareness. Meaning that you know what your main issue has been in the past, and knowing this can help you focus on choosing better in the future. And let me say, your baggage or problem is not that you love too quickly. Love is great! Feelings are meant to be felt! What’s more important is the part where you say you see the signals of the profoundly wrong men and you ignore them.

As for the guy who just wants to be friends, ooh, girl, how many times did I hear that one from guys myself. I feel like it’s a curse for women who are out to accomplish things and kick ass in life—we seem more like business parters and buddies to people than romantic options right off the bat. But I’m not saying to accomplish less or act like someone who does! Instead, I would suggest you keep being exactly who you are, and then work on this one thing: Accepting a different future than you pictured.

I don’t know if you have my book or read it (the Meeting Your Half-Orange one), but it’s what I talk about on page 57: How I told my Mom that I had decided that I was ready to wait for the right relationship as long as it took. That, essentially, I’d rather wait 10 years for that love of my life and have children another way (get pregnant on my own or adopt), than to settle down with someone who I felt “eh” about just to have someone there. There was something so freeing about making that choice, and for me, this was the major turning point of my love future. Acceptance of a life different than I had pictured for myself.

This is also what a friend of mine did this year, who I’ll call Britta. She was 39 and feeling potentially doomed herself, because she wanted a relationship and she wanted kids. And the pressure to get the first fast enough so she could have the second was wearing on her. So, Britta did what women are doing these days: She made an appointment for a fertility specialist, got things checked out and the thumbs up that she was healthy and ready to conceive, and then she set a date for herself: It was October when she said, “If I haven’t met anyone by March, I will go to the specialist and get myself pregnant.” Then Britta planned a big trip on her own to surf in Costa Rica for two weeks in February, right before she was going to conceive. When she got back, a couldn’t-turn-down work project came up that took her into April, and as she was finishing up her project, she was set up on a date with the guy of her dreams. Well, it took her three dates to realize this, but when she did, she was blown away. Not only was he a perfect match for her, but he had a kid of his own and wanted more kids. True story. And they’re happily in love and working on that baby. Her turning point was the same as mine: acceptance of a life different than the one she pictured for herself.

So I suggest this more than anything. Think about the future you’re picturing, then re-adjust it. See what would happen if life rolled out a different carpet for you. How could you still be happy if it did? If you found out you would meet the love of your life at 38, what would you do right now to be happy until then? The minute we let go of the steel rod we like gripping onto for dear life of exactly the future or person we want, the minute we take a step off of the concrete path we think is leading straight to what we know…that’s when life surprises us and sends us the person we’re actually supposed to be with, and the life that’s even more interesting than the one we’d written up in our heads.

Keep doing what you’re doing and being who you are, laughs and all! But let go of THE PLAN. And find a way to make a statement to yourself that you’re okay with a different route or a new story. Find a way to be happy right now with what you have in front of you, and you’ll not only be happier, but you’ll find yourself attracting more of the people who are right for you. And then, of course, if they send you signals otherwise, pay attention and for goodness’ sake, run! 🙂

Big love,

“How do you know if someone is really your half-orange and how soon can you tell?” —R.

Hi R.,

Ask your gut, which I like to think of it as asking if your two major systems see a “Go.” Your gut is like a perfect blend of your emotional half and your logical half. If your emotional half is gung-ho about it, you can check in with your logical half and look at it from that point of view: Is he a good fit for you? Will he keep you safe and look out for your best interests and allow you to be your best self, and be a good partner as you go forward? Do his morals and his drive and plans for life match up with yours?

If you happened to make that Big Love List I wrote about in Meeting Your Half-Orange, where you address how you want to feel in a relationship , go through that list and see if it matches. If you want to feel smart…does he let you feel that way? If you want to feel sexy and funny…does he let you feel that way? If you want to feel protected and safe and taken care of…you get the idea. (If you haven’t made a Big Love List, go to my OPTIMISM WORKSHOP: Your Big Love List and whip one up!)

If your heart is in, now is the time to step back and see if your brain agrees. It may find little things that don’t matter (“I pictured a guy who wore better shoes”), but if it finds things that are more serious (“Hmm, he talks an awful lot about stealing from his friends”) it’s worth a serious debate.

You can know someone is your half-orange pretty quickly. Or, it can take a minute to realize a gem you have in front of you. There is no hard, fast rule on timing. Your gut will know. Ask it.


“I just ended a relationship with a bad boy, and started dating a nice guy who has all of the stability and lovely qualities the bad boy was lacking. The problem? I’m not physically attracted to him. I don’t get excited when he calls and even though we did have sex finally, I don’t want to do it again. Is there something wrong with me? Am I looking for the wrong things? Amazon also recommended Lori Gottlieb’s book which gives the exact opposite advice from yours, which is to settle for Mr. Good enough, but the thought of settling depresses me. Should I settle for a nice guy I don’t really like?” —K.

Hi K.,

Your story about the bad boy and good guy are so familiar — we have all been there, tugging between the two of them, wondering which one’s right for us. Well, I’ll say this: By the sound of it, the bad boy sure isn’t right for you. If he’s not providing the feeling that you’re loved and important and taken care of and special, than forget him. You deserve a good guy like the one you’re talking about. But here’s the shortest answer I’ll give you: Just because one particular guy you’re dating is a good guy does not mean he’s the right good guy.

What I read is that you’ve proven to yourself that you can like a good guy. The fact that you took it five dates far and slept with him and see all the potential for a happy relationship with him? That’s huge! That’s progress! I’ll bet that when you were with the bad boy and saw this guy (or guys like him), you didn’t consider those guys as even options for you. So I say kudos to you for doing those visualizations and imagining how good it would feel to be with someone who actually put you at the top of their list and who considers you special.

That said, you don’t have to settle down with the first good guy who makes you feel that way. There are a lot of good guys out there, and the fact that you’ve started dating one is what I call in Meeting Your Half-Orange “the little green sprout.” The fact that you’ve gotten yourself one big step closer to enjoy the company and picture a future with a guy that treats you well? That’s amazing! Don’t get down because you don’t want to have sex with him again; stay up that you’ve come this far with him in the first place. It’s a sign you’re closer than ever to being ready for the right good guy. Maybe it’s him, but I don’t know.

I mean, just read your own words again: “I am not physically attracted to him. I don’t get excited when he calls and I even though we did have sex finally, after our fifth date, I’m not sure I want to do it again.”

The fact is, there is nothing wrong with you. And while I can’t say whether or not you’ve been looking for the wrong things—or have over the years—it sounds like you know now what is important, and that’s all that matters. As for Lori’s book, she makes some good points about finding the important stuff in a guy, about looking for the yes’es, and I couldn’t agree more. But she also pushes the idea that even if you don’t feel a spark or special about the the person you’re with, maybe it’s worth settling anyway and with that, I couldn’t disagree more.

I know that you’re scared because you’re 38 and you want to be in a relationship, but don’t let fear make this choice for you. Do you really want to marry and have children with a man you don’t want to have sex with more than once? With someone who doesn’t make you want to take his call? If you don’t get excited about going out to dinner with him or kissing him now, then what’s going to get you through the ups and downs of a relationship as time goes on? Determination, I suppose. But that doesn’t sound like a very joyous existence to me. And haven’t you waited this long because you want a relationship that enhances your life, rather than bringing it down?

The point of a relationship is supposed to be to add to your life, to make you even happier than you are when you’re single, to perhaps start a family with someone and have fun along the ride of life together as a team. Otherwise, why get into one? But it sounds to me like this guy—so early in your courtship—already isn’t making you happier. He’s making you have doubts. He’s making you question yourself. He’s making you wonder if there’s something wrong with you because you don’t like him.

The truth is, sometimes even the hot sexy guys who look good on paper don’t cause a spark in us. And I hate seeing awesome, strong, gorgeous women beat themselves up because they can’t “make” the chemistry experiment sizzle, they can’t make the volcano work. And the way I see it, without a spark of something, it’ll be hard to make a relationship work. I’m not saying that your other half needs to look like that bad boy and needs to be physically perfect from the outside, but *something* about him does need to elicit a spark of *something* inside you that makes you feel lucky to be with him.

For those who’ve read Meeting Your Half-Orange, you may remember the story of the girl who was best friends with a guy who was balding and wore concert T-shirts, while she’d always pictured someone with higher-end style. Yet when he kissed her one night, the sparks between them flew, and she now considers him the hottest guy ever. The way she put it was, “I’d look at him and say, ‘I’m so glad it’s you.'” Her friends didn’t necessarily consider this nice guy hot and the general public might not, but for her, he’s the cat’s pajamas, and it’s because of how big his heart is, how he makes her feel, and because their physical chemistry—once they tried it—turned out to be electric.

This guy you’re dating, maybe you will fall in love with who he is on the inside. And maybe he will turn out to be a great match for you. But I don’t want you to torture yourself with trying to find it inside him if it’s just not there. My good guy friend just finally gave himself the gift of ending a relationship with someone he kept “trying” to make it work with. He said “I was so exhausted because I didn’t want to *try* anymore, I wanted to just *be.*” And that’s how the right relationship will make you feel. You’ll enjoy being, instead of working so hard trying.

I can’t tell you what to do, of course. This is your life, your heart, your future. But it sounds to me that you’ve finally figured out how you want to feel in a relationship with a good guy, and it’s just now about summoning the right good guy. If “settling” depresses you, don’t do it. You don’t have to! You know what you want now. You can follow your gut from this place forward.

You don’t have to dive into my book if you don’t want, but the truth is, I wrote it for people precisely like you, because you are now where I was when I was dating. I was tired of beating myself up for not liking the “right” people, I was tired of trying to summon chemistry with good guys, and I was tired of dragging myself around to places where I might meet the right someone. What I did, and what you can do if you’re up for it, is simply begin by realizing you’re not asking for too much. A good guy who you’re also attracted to in some way? That’s simply a combo of two men you’ve dated before, and these men do exist. The guy for you may not be a Versace model hot, but it is possible to be madly attracted to a guy with a kind heart who treats you like gold! You just have to believe that guy does exist. I believe he does for you. Now you just have to believe it. That’s all that optimism is—believing it. Maybe it will grow with this guy, but whatever happens, give yourself permission to feel a true connection. Because that’s what’s going to make you happy in a relationship in the long haul.


“I just picked up your book. This year wasn’t one of my best and I’m committed to do everything to find a long-lasting relationship. After skimming through the book, I’m really excited to start working on the points you bring up, but there is a problem. I’m a guy. Does the advice work for the other half of the population?” —P.

Hi, P,

Yes! It does. I know it seems a little tough to break through the pronouns of me talking straight to women sometimes, and if I could do it all over again, I would speak directly to you men, too. Because the message itself is for everyone—every gender, every age. The most important element is the science, and the science is the same. The impact that we have with our thoughts on our emotional brains and how this affects our body language and the energy we give out and what we get back from people—it’s universal.

I have heard from a couple guys who said they hard a hard time looking past the female-aimed message. But I’ve heard from more who said they were able to filter that stuff out, and it has totally helped. One guy who read it wrote to say that he started doing some of the things in the book one day (he walked to work, went a new route, spoke to people he normally wouldn’t, and worked up an Orange Buzz) and by the time he got home from work that night, two women he liked were calling and texting him and he was freaking out about how it was clearly all about the new energy he was putting out there. He said that  one day after reading the book, he had changed from feeling tired and defeated in dating to being excited and confident. I also had a married guy friend read it and he’s been using the principles for success in work.

So if you’ve had a rough summer and could use a boost in some way and since you already have the book, I think you should give it a shot. Laugh off the parts that are written directly for women (while also, perhaps, gaining a little insight into the female mind about how we feel and think?) and try to take in the neuroscience and the studies from psychologists. It’s powerful, life-changing stuff and I would love for you to have the chance to get to the meat of it and let it start working for you.


“I was dating a guy on Match.com. He would call three times a day, we would have amazing dates and then he asked me to be exclusive. Then he got distant, moody and unresponsive. He said we should break up while he worked out what he wanted. Two days later, he was back on Match. I feel like an idiot and can’t stop thinking about what went wrong or what I could have done differently. It makes me not want to date anymore.” —T.

Hi T.,

Aaargh, that sucks! I hate thinking about that stuff: the mysterious guy who is all over you and then—POOF!—disappears. I met so many of that guy throughout my dating years, too, and it’s frustrating as hell.

As for you feeling like any of it has to do with you, you’re not an idiot and there’s nothing you could have done differently in that situation. It’s simply like another level on that crazy game show Wipeout, where you have to get punched a few times on the dating platform to get to the next level.

What I will say is this: You’re too good for letting this one guy knock your game down. You’re so much better than taking some lame loser guy’s opinion of you and letting it color yourself in any way. The only thing you should be thinking about is how you feel about you, no one else. No guys, no friends, no bosses, just what you think of you.

Since you sound like you’re exactly where I was when I was single, it’s time to start thinking about what you can do to make yourself happy this month. For the rest of the month, don’t think about the guys you’re going on dates with, or the guys who aren’t emailing you on Match, or the guys you like but aren’t sure how to make them like you (we women can plot for years on that one!). Instead, think about what you can do in the next month that has nothing to do with guys that will make you gloriously, ridiculously, incredibly, laughably happy. Once you see yourself worth it again, you’ll start attracting the right kinds of guys again and be back on the path to your half-orange.

That’s my advice anyway. If anyone else has any other ideas for T. pass ’em on!