Dear Lovely: Girl Afraid of Rejection

*Dear Lovely,

I have been reading your blog for years. I love everything you write and I can honestly say your words have changed my life. I am a completely different person than I was just three years ago. But, I think I am ready to date again after putting a lot of work into myself and being single for over a year now. I can’t say I love my single life all the time, but I can say, it has been the most peaceful, calming, happy time of my life that I’ve ever known (no obsessing over why he didn’t call, wondering if he was out, etc). But, it has been very lonely at times. From time to time it does cross my mind to go run out and just have some one-night stand or call him back. I can’t tell you how many times I picked up my phone to text him or call (but I didn’t!!! I made it through every craving!)

Anyway, not to waste your time, there’s this guy and I think he’s really healthy. And I can’t really see any red flags. He’s got a good job, divorced, no kids and we like a lot of the same stuff (hiking, surfing, triathlons, etc). We laugh a lot and have spent a few hours together, not alone, but with friends over the past several months and I think we really click. But, he hasn’t asked me out and so, I wanted to know if you think it’d be a good idea for me to ask him out. Thing is, I am scared to death. Scared he’ll reject me. Scared I’ll look like an idiot. And worse…scared that I will start to obsess again. Obsess if he says yes, and obsess if he says no. Coming out of love addiction, how on earth do you find and have a healthy relationship?

Thank you so much,

– Girl Afraid of Rejection


Dear Girl Afraid Rejection,

For starters, I am happy that you got over any fear you may have had in reaching out and asking for advice on something that’s been bothering you. That says a lot about the person you are. Strong. Determined. Not afraid to seek help from others. Pat yourself on the back.

After you do that, hug yourself for devoting a year to your singlehood. Woohoo! Too many women fail to see the divine benefits of being single. My one biggest regret was not spending enough time alone in between my last avoidant boyfriend and my one and only healthy boyfriend, who eventually became my husband. Four months wasn’t enough to explore the world without answering to anyone but myself. And so, whatever happens with this guy, if you end up single again, continue to embrace it. It’s a time in your life that you won’t always have access to. I just want to put that up front.

As for my advice to you—I could easily start off by telling you, “Take the risk!” “What have you got to lose?” and “If you don’t ask him out you’ll never know!” But, I hesitate. Those responses are designed for people who know what to do with both success and failure. They belong not only to people willing to take risks but who recognize that risk often means a risk taken in vain.

Are you there yet? If you’re not. You need to rebuild yourself to be there.

So, let’s play this out: if he says yes, are you ready to also be healthy and responsible and grown-up and loving and fair? (If he, indeed, is all those things as well). Are you healthy enough to no longer be in denial over any possible red flags that aren’t showing up now, but might three months down the road? Are you strong enough to create healthy boundaries if necessary? Play it cool? Not “fall in love” too fast? Ditch the fantasies of marrying the guy after date-two? Enjoy the organic nature of what may or may not come of the two of you connecting. Walk away if something doesn’t feel right?

Are you there yet?

How about if he says no? Are you ready to deal with the wallop of rejection and all those pesky underlying things, underneath the fear, that might actually rise up and get worse if you ask him out and he says no? Those monsters inside us all that grab us by our throats and tell us we’re no good: inadequacy, loneliness, abandonment, failure, desperation?

Are you there yet? Are you able to say in the face of possible rejection, Screw you, failure. He may not be interested in me, but that does not mean that I am not worthy. 

When we decide to play the dating game, we don’t have to be perfect. We don’t even have to be “normal” or fully “recovered” from our last relationship. But we do need to be in a place where we can soothe ourselves no matter what he says. No matter what happens.

Because part of the risk of connecting is knowing that not connecting might be a possibility. Thomas Edison made 1,000 unsuccessful attempts at inventing the light bulb. He never gave up. He never not thought he wasn’t worthy enough to figure it out.

So, whether you decide to wait for him to ask you out or you ask him, be brave. Be courageous. But lose the expectations of a fairytale. Stop mapping it out in your head what’s supposed to happen next. Keep being your happy, single self—which by the way, is never, ever, ever fully absent of loneliness, frustration, anger and every other human emotion (spoiler alert: single, married, living together, you will still have the full range of negative and positive emotions).

And here’s something else. There’s a great little Buddhist mantra that I use every time I get on a plane to deal with my anxiety. “Relax. Nothing is in control.” In fact, that is the very place I put my head and my heart when D came along. I was so tired of dating. So tired of rejection. So tired of meeting Mr. Wrong, that when D asked me out on our first non-date (he came to my house with a coconut cake and we sat in my living room talking until 4:30 in the morning) I was kinda like, whatever. I wasn’t jaded. No ma’am. I was simply absent of need. And therein lies the mystery problem. Need. Need can be sniffed out by the opposite sex like a dead bird to a dog on the hunt. You can try to hide, stuff, disguise it, and yet, it’s still there. But all hope is not lost! Fill yourself with gratitude for what is right in front of you right now. Take a good hard look at what you have right at this moment. It’s all you got in this world and it’s worth more than you’ll ever know. After you do that, then go ask Mr. Healthy out.

Last but not least, from your current vantage point this guy may “seem” perfect to you. And “clicking” may seem like the perfect springboard into a dreamy romance. But clicking and enjoying a few hobbies doesn’t make a strong relationship. It makes a great beginning. The hard work of figuring out if the two of you are right for each other comes later. But…you’re not there yet. You’re right where you should be. Nervous. Happy. Giddy. Filled with hope and scared to death.

If he says yes, your job isn’t over. And it really hasn’t begun yet either. You’re in limbo. And your object is to simply enjoy him, keep an eye out for red flags,  completely and utterly deny yourself any fantasy or expectation about what might happen and focus and refocus on the “what I have right now without him” stuff. This should tame the obsessing.

If he says no, your new job is to figure out a way to deal with the pain of rejection through healthy coping mechanisms. I.e. run a marathon, bake cookies, cry, write a book, go fishing. Understand that rejection is a good thing. Just don’t chase after him. Don’t say, “Poor me.” And don’t jump into the next quickest relationship simply to avoid dealing with the pain and loss of this one.  If you can do that, you are 200,000 steps closer to being a superhero. Let me know what happens!


Truly yours,


Got a question? Need advice? Ask Lovely @


*I get many letters every month asking for my personal advice. I thought I’d start sharing them, with the writer’s permission, of course.  Disclaimer:  I’m not a therapist. I have no professional titles. But I do have one thing a lot of pros don’t. At least 10,000 hours devoted to really bad relationships that I somehow learned to stop having. 



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