Take a look at the letter one person wrote to their younger self:

I stumbled across it on, oh yeah, StumbleUpon. (Um, hello, did you know they have an App now? It’s awesome.) This quote is from the site Dear Young Me that’s also on Twitter (@DearYoungMe). The gist? People submit notes they want to write to their younger selves, full of the advice they wish they’d known then.

I love this particular letter because it’s something I wish I told myself, too! When I graduated from college, some of my friends were already planning their weddings. Four years later, another batch of gals got married. And with every wedding, the “singles table” got smaller—but I was always sitting there, without fail, wondering when my time would come. I kept worrying: Why aren’t I getting married like everyone else? What’s taking my love so long to come?

Well, now that I’ve found my half-orange, I know the answers. I know why I wasn’t getting married back then: Nothing was as good then as it is with Gus! And I know what took my love so long: He and I both had to grow into the people we are today, who could appreciate and love one another for who we were, fully formed, confident and happy.

Don’t worry about everyone else’s timeline! Suck it up, shell out money for their wedding presents, and sit back with confidence. Know that your love will come when it’s good and ready, so you may as well enjoy the singles table at their weddings. Make the most of it! Live up these weeks and years, because you won’t be single forever. And when you’re finally hitched, you’ll want to write a letter to your younger self begging that you appreciate what you have right now.

Browse through Dear Young Me for more inspiration. My advice:

1. Write your own letter to your dearest younger you so you can see how far you’ve come in life and love. I mean, really, look what you’ve learned! Look at the people you know well enough not to date anymore. Look at the lessons you’ve learned about yourself, about what you like, appreciate, can tolerate. And…

2. Really listen to those who have lessons to pass on from an older, wiser place. Sometimes it’s best to learn our own lessons in life. But sometimes, hearing what someone who’s been through it has to say can really help.

Think of what you’d tell your younger self. Then, listen to the older, wiser you. And take your own advice!

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Big love,

Now, I don’t know who made it, but I got it from this StumbleUpon link if you want to check it out.

Like the image says, you’re amazing. And you will be picked by the right one who’d brave enough to make the climb.

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Big love,

Bill Cunningham is the photographer who shoots and compiles the On the Street page for The New York Times Style section each week as well as “Evening Hours.” And if you don’t know him (as I didn’t), well, he’s not who you’d expect to be on the pulse of fashion trends.

Bill is 80 years old (or just past that), spent the last few decades of his life living in a small box of a studio room at Carnegie hall with the bathroom in the hallway, and rides his bicycle through New York to capture what he sees. The reason I loved this film so much wasn’t in the fashion, it was in the heart of Bill Cunningham. He’s the rare breed of a person full of heart, truth, passion for his life and work, and a truly honest and good soul. I cried a few times in the film not because anything sad happened, but because I was moved by how good a person he was.

How will seeing this film help your dating life? It’s a call to live your life as your authentic self. If you want to live in a box, do it. If you want to ride a bike to work, do it. If you want to wear a blue jacket every day for the rest of your life, do it. And if you want to be like Bill’s favorite subjects who wear purple feathers and polka dot suits and show-stopping hats for a stroll down the street, do it. Be who you are, follow your passions, and live your life as only you can. If you want to go for breakfast on a date instead of a dinner, do it. If you want to order dessert for an appetizer, do it. If you want to skip away from a good date as happy as can be, do it. And if you’re on a date with an obnoxious cad and you want to get up from your stool and say, “You know what? It’s been an experience meeting you, but I have some friends to go see,” do that, too.

Bill lives life his own quirky wonderful way, spending his days and nights celebrating true authenticity. He finds beauty in being yourself. As he said in a speech at a gala given in his honor in France:

“It’s the same today as it ever was. He who seeks beauty will find it.”

Go see Bill Cunningham New York and let it inspire you, too.

Big love,

Dating advice from this documentary? Who knew?

I finally got to see The September Issue, which has been on my “to see” list for a year now. You know the film, right? It’s the documentary about the making of Vogue magazine’s September 2007 issue. It follows all the major players, including editor in chief Anna Wintour and creative director Grace Coddington. And I was so taken by the talents and attitude of Grace that I wanted to share two things she said in the film that can help you in your love journey as a dating optimist. Your two very Vogue tips for love:

1. Embrace being a romantic!

When Grace was in Paris for work, she took a side trip to the Palace of Versailles. As she looked out into the garden, she quietly took in the view and said this:

“It’s beautiful. I think I got left behind somewhere because I’m, you know, still a romantic.”

I meet so many people—women especially—who scoff at the word “romantic.” Heck, I was one of those women. I used to say I didn’t want cliché flowers and dinners on Valentine’s Day, that I didn’t want a nice engagement ring, that I wasn’t about holding hands and using nicknames and showing PDA and other ooey gooey love stuff. But now that I’m with my half-orange, I’ve realized something: Believing “romantic” doesn’t mean you embrace Hallmark cards and candlelight dinners. It means you’re open to life and open to love. I think the more “romantic” you are in life, the greater your opportunity to have love.

How can you be a romantic in life? Believe in hope, believe that there is vulnerability and love in all of us and that bad situations can be handled by shifting our perspective and embracing the good within it. Believe in quiet moments where you listen to birds chirp and smell fresh cut grass and feel the wind on your face. Believe that even a bad date can be salvaged by finding what’s worthy or interesting or hilarious about the person you’re with or the situation you’re in. And believe that you—that we all—deserve a great love in life, a teammate to travel the journeys of life with. Be a romantic. Find what’s beautiful at the Palace of Versailles or the view from your own front door, and be open to the beautiful experiences life has to offer.

2. Forget about perfect—we’re meant to be different!

After Grace styled a “color blocking” fashion shoot that featured a profile shot of the documentary cameraman Bob, Anna Wintour apparently looked at his little belly in the printout of the shot and joked to him that he needed to go to the gym. When Bob told Grace this, she scoffed. This is what she said:

“Personally, I think it’s better that you’re not, like, skinny skinny. I really do. To me, it much more makes the point that you’re real people and not models. Everybody isn’t perfect in this world. I mean, it’s enough that the models are perfect. You don’t need to go to the gym.”

There again, Grace nails it. There’s enough “perfect” out there with all the Photoshopped ads, plastic-surgery pumped up people, and graphically enhanced characters we’re faced with every day. Our aim in life shouldn’t be to mimic that. We’re all different and we’re all meant to be different.

So if you find yourself grumbling about some physical aspect of yourself that you worry no one will love (that mole, those toes, that crooked tooth) remember that your half-orange isn’t looking for a picture of perfection. Your half-orange is looking for a fun, fabulous life-affirming love. With you. Yes, stay healthy, live your best life. But you don’t need to work off or Photoshop out every “flaw” you think you have. Your half-orange is going to love you just the way you are.

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Big love,

Use your picture to your authentic advantage!

For the survey, OKCupid asked millions of users to rate other people’s attractiveness based on their photos, and then analyzed the settings of the cameras of the photos themselves. How cool is that, right? Which means that armed with information on things like what time of day the pics were shot and with which lens, etc., they noticed some trends.

Here’s my take on some of what they found as well as my own thoughts: overall, four great tips to taking a photo that will help attract your half-orange.

1. Take photos in late afternoon sun or early evening twilight. Psychology Today notes that the lighting at that time of is more flattering, and it’s true: it creates soft shadows which creates more a slimming effect. It’s different than the harsh shadows created by bright sunshine. If you want to take a photo on a bright sunny day, just try doing it in a soft shadow of a tree or patio umbrella to create softer shadows.

Me (far right) with my gorgeous girlfriends. I took this from that "slightly-above angle."

2. Take the photos from a slightly-above angle. This is a tip of mine that works every time. Now, I don’t mean holding the camera above your head, but if you have your friend hold the camera at, say, their forehead level and tip it down toward you…hello gorgeous! It creates a slimming chin definition that takes away those double chins and hating your neck like Nora Ephron does. And there’s something about how your eyes end up looking slightly up at the lens rather than straight on—kind of adorge. I do this with all my shots of my friends, and I’ve been crowned the “staff photographer” for the flattering pics we get because of it. That picture (at left) is a perfect example.

3. Post a happy late-night photo. The OKCupid study found that late-night photos got stellar ratings from viewers. They couldn’t pinpoint exactly why that is, but consider the fact that many late-night photos are taken either with or when you’re among friends, which puts you in exactly the state of mind you want to be in with your half-orange. And, sure, sometimes you’re a cocktail or two into a night, which relaxes you more and probably brings out a much more natural smile—and as I talk about in Meeting Your Half-Orange, it’s that natural smile, the one that makes the corners of your eyes crinkle up, which feeds information to your emotional brain that you are truly happy, which affects the energy in and around you. And that stuff gets picked up in a photo, boy. So consider that: If you are trying too hard to get a flattering photo in the daytime, get someone to take a snap of you at night.

4. Be real. The three tips on taking a good photo are all about planning or altering the angle of the shot so you look your best. But even then, a photo won’t mean squat if it isn’t reflecting the real you. The way I see it, a fake-ish photo is not only setting you up for disappointment (because you may be disappointing your date if you’re not really the person you sold yourself to be), but it also isn’t building you up in the right way. You should be proud of yourself for who you are, not who you wish you were. If you don’t ski, for example, posting five shots of that one trip you rode on the ski lift three years ago isn’t so straight up, is it? And if you have a few smile lines or wear glasses, posting the one shot of you that’s kind of far off at that fancy event where you once wore contacts with your friend cut off at your side…again, that’s not the real you, is it? If your potential dates don’t like you for who you really are—your likes, your dislikes, your desire to have kids, your freckles and glasses—then you don’t want to be dating them anyway!

So post the most flattering shot you can of the real you in a happy state of mind, and you’ll be one step closer to your half-orange seeing you for the awesome partner you plan to be.

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Big love,

You have two choices when you're single. Choose the path of "more." (Image by Amy Spencer)

“I haven’t been able to find what I want in love, so I guess I’m wanting too much.”

“The road you should take isn’t the one in which you want less,” I said. “The road you should take is the one in which you want more.”

“More?” she said. “But I haven’t gotten any of it yet, so why would I ask for more?”

What I told her is what I’ll tell you: If you take the road in which you ask for “less” in love, you’ll be less excited about getting it, which makes you more negative and less hopeful in life—less of yourself. The less you are, the less you get.

But if, on the other hand, you start upping your wants, you start getting excited about getting it all, which makes you more positive and hopeful in life—more of yourself. And the more you are, the more you get!

Dating optimism is about using your energy for the best and creating a buzz inside of you that radiates out to all the people you meet, drawing in the most positive things around you. The stronger your buzz, the more you’ll be led in the right directions: You’ll want to pop into the smoothie shop on the way to work, and you’ll want to get together with that new friend for a glass of wine, you’ll want to hit that lecture you got a mailer for at work. The greater your buzz, the more you’ll feel inspired and hopeful, and the more you’ll choose the experiences that will lead you toward your healthy relationship.

So. If you ask for less than you want in love, how big will your buzz be? Not very. But if you ask for more in love, you can build off your excitement and bring you all you want. Choose the path of more: Ask for a partner who listens, likes you, makes you laugh, and thinks you’re brilliant and sexy at the same time. With buzz like that, you’ll be heading closer to love, not further away.

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Big love,

Happy Friday, people.

If you’re a single parent, I contributed to a new Parenting.com story that’s chock full of my dating advice for you. Even if you’re not a parent, there’s some insight here about where to meet the right partner and just how honest you should be on your online profile (it’s all about where you focus the lens as you tell the truth). I think it’s pretty good stuff, but check it out and see what you think.

Plus, if you don’t yet have a copy of my book, or you really want another to give to a good friend who could use a dose of the orange buzz, check out this fun Parenting.com Book Giveaway. Just share your worst or funniest dating disaster and you’ll be entered to win.

And while you’re at it, enjoy the dating success story of single mom writer Christine Coppa. But I warn you, her posts are addicting…

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Live, people, live.

Big love,

I wanted to share this story I just came across from writer Abigail Pickus, who writes a column for The Jewish Week about her dating life called “Abigail in Love (maybe).” In this column called “Am I Still a Dating Optimist if I Throw Away All of My Dating Books?” as she talks about reading my book as well as others, I think you’ll appreciate her frustration with not just dating, but dating books that tell you how to do dating right.

In the end, Abigail says she’s decided that because even Meeting Your Half-Orange, which she liked, doesn’t have the formula for love, she’s going to live her single life without dating books from now on. As she writes:

“In other words, people, I am done with all the dating books. Even the nice ones. From now on I am only reading books that are going to engage my mind and imagination – not give me another formula for finding love. That I will just have to leave to fate.”

What do I love so much about a cool woman who isn’t saying, “Run and buy this book”? That, inadverently, she’s come to the conclusion to live her life in the way I want all of you to. She’s not going to obsess over her dates and her single status. She’s not going to scan online for advice on how to flirt her way to marriage. And she’s not going to buy a book a week on how to change herself for the right guy. Instead, she’s going to read and do things that engage her mind—in other words, she’s going to engage in what Meeting Your Half-Orange readers know are “gratifications,” those activities that make you feel smart and strong and fulfilled. Follow Abigail’s lead and make those same day to day choices for yourself that lead to eudaimonia, the gratifying happiness of being satisfied as your true self.

If you’re feeling like this writer and want to just toss your books into the trash, go ahead and do it! (Be gentle with mine, though, would you?) Then start fresh by living your day to day the way you want to. Read the books you want. Watch the movies on your Netflix list. Make the vacation plan you’ve been putting off until you met “the right person.” The more you live life as your true self and the more truly, eudaimonically happy you are, the better the energy you’re putting out there, and the easier it will be for your half-orange to recognize you as the happy, kick-ass person you are.

Big love,

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Like the snow monkeys we saw in Kyoto, they can help each other because they're capable themselves. (Image: by Amy Spencer)

Either way, as foggy as I’m feeling, I still wanted to share a quote I came across this weekend from author Tom Robbins (he wrote Jitterbug Perfume and Even the Cowgirls Get the Blues). He said something so wise about what people should and shouldn’t look for in relationships.

“When we’re incomplete, we’re always searching for somebody to complete us. When, after a few years or a few months of a relationship, we find that we’re still unfulfilled, we blame our partners and take up with somebody more promising. This can go on and on–series polygamy–until we admit that while a partner can add sweet dimension to our lives, we, each of us, are responsible for our own fulfillment. Nobody else can provide it for us, and to believe otherwise is to delude ourselves dangerously and to program for eventual failure every relationship we enter.”

I know it can sound like a broken record sometimes to point out out that we need to be fulfilled in our own lives rather than looking for someone to fulfill us, but we still look for short cuts. Smart, successful people do this all the time. We feel we have great lives of our own, and yet we sneak in these lazy little wishes. You know the ones: Wishing for a healthy partner who will kick you in the butt to be more active and exercise more. Wishing for a rich partner so you can take a break from worrying about bills. Wishing for a social partner who will make you more outgoing.

But like Tom Robbins points out, looking for someone to fill those voids never, ever works. Because we’ll always find new voids and new reasons why this one person isn’t fixing or filling in where they should. The answer? Fulfill yourself.

We all need to create the lives we want for ourselves—be it full of money, adventure, exercise, travel, drive, family—and then, once we feel great about who we are and what a good partner we’ll be for someone else, then we look for the partner to share life with. We’re responsible for our own fulfillment. A relationship is about joining two fulfilling lives together, where each person can share and be a part of the great lives they’ve built and will start building together. The more together you are, the more you can bring to the relationship. How can you be strong for your partner if you don’t feel strong within yourself? How can you support your partner if you’re not in control of yourself? How can you help your partner laugh if you’re not already smiling yourself?

Tom Cruise had it all wrong in Jerry Maguire when he said, “You complete me.” Your half-orange shouldn’t be the person who completes you. You should complete yourself. Let your half-orange complement the fulfilling, wonderful life you’ve created for yourself. The more fulfilled and happy you are, the more right your relationship can be.

Big love,

Gosh, I love embarrassing questions. Mostly because the questions that people think are embarrassing really…aren’t. When I hosted the Sirius radio show Sex Files on the Maxim channel, I used to get calls all the time from people saying, “You’ve probably never heard this one before, but…” And the thing is, I usually had. Because we’re all human, and our experiences—good, bad and embarrassing—are so often similar.

A new book from Health magazine

That’s why I’m such a fan of the new book that one of my favorite editors—Lisa Lombardi at Health magazine—co-authored. What the Yuck? is full of those questions people are afraid to ask but secretly all want to know.

Now, in honor of those “You’ve probably never heard this one before” questions, I’m going to answer one of them right now. (I also regularly post answers to other questions that have been emailed to me in the “Let’s Talk” Q&A section of this site, so check some out!)

The Question:

“You said never to say never…but this one “never” is hard to argue with: I’ve never been on a date, never been asked out, and, as the movie goes, never been kissed. I just finished reading your book. You might wonder why I read your book if I haven’t had any dating experience yet. I’m almost 24 years old and am truly at the point in my life where I want my half-orange to find me. I am becoming the person I want to be: I recently took up competitive running, lost a good amount of weight, and am now starting to enjoy my life as a graduate student. I want to be a dating optimist but I find it extremely hard when, as far as I know, no one has found me date-able. I find it very hard to believe that any man will be able to love me. I know that I need to banish those thoughts but after this long, it’s extremely difficult to do.” —R.

My Answer:

We’ve all had our “never” times, R. There’s no such thing as a rulebook for how fast or slow people are supposed to go. And by the sound of it, you’re going at just the right pace or you.

I’m so happy for you that you say you’re becoming the person you want to be. And that, I must say, is the best thing you can do for your dating self. Because the more you know who you are and what you want in life, the better you’ll approach future dates and potential partners. Now, as for no one finding you date-able…psshaw! (You get that sound effect, right? I’m waving away that idea as nutbaggy!) You are date-able. You are loveable. You will have a wonderful partner in your life who won’t be able to fathom that you deem him worthy to be with you.

And the first step I think you should take to meet that person is to go on a date. Yep, pull off the Band Aid and get on out there. The easiest and best idea I can suggest is online dating, because unlike a bar or a party or a restaurant, all the people you find on that dating site are there for the same thing—to date! Don’t disguise who you are, don’t put up a photo that doesn’t look like you, don’t say you like things you don’t like because guys might like it. Check the box for “want a relationship,” wink at a few people, and have fun. When someone asks you out, go for it. He doesn’t need to be perfect, he doesn’t need to be your future husband, he just needs to be someone who wants to have a coffee or a cocktail or a meal on a cool fall night over good conversation. That’s it. If you know a friend who wants to set you up, or another place to meet someone to date, go for it.

My point is, dive into a date. First dates are notoriously awkward anyway—whether you’ve had 30 first dates (oh, look at that, another Drew Barrymore movie) or none, so you’re not going to stand out for being inexperienced, trust me. Just go with the idea in mind that it’s nothing serious and that this first date or your first kiss doesn’t need to be the be-all, end-all—you’re just breaking that ice and taking the first step into the rest of your dating life. And you can always keep in mind my favorite mantra: The worse it is, the better the story.

I hope that helps, and I hope you can get your optimism up there. Life, remember, is all about first steps. You’ll be taking first steps when you’re fifty, too, so enjoy these first steps into dating and be confident that because you will have a happy ending, you can enjoy the whole ride along the way.

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Big love,