Advice

We all set goals and make plans in our lives. After all, without a plan in place, it would be difficult to accomplish anything! But sometimes our planning and control mechanisms go into overdrive. For instance, maybe you try to predict others' reactions to your news about starting your own business and plan what you say or do in response – before they’ve even said a word! Or maybe you think of everything that could possibly go wrong so you can feel more prepared. Or perhaps you have a set time schedule – whether it’s how many errands you can run in an hour, or your plan to get your MBA by age 25 while working at your full-time demanding job.

And chances are, things didn’t quite go as planned. People can be unpredictable in their reactions. Ordinary plans get hijacked by extenuating circumstances, like traffic jams that hold us up. Or our job takes us to a new city, and our good intentions for school get put on hold.

When you’re planning out your life, to accomplish everything by a certain age, you can expect that life probably has other plans for you. Life will interfere. And the beauty is, that is okay. It is supposed to be that way.

As cheesy as it sounds, life is a mystery. We don’t know how long we will live, what experiences we will have that affect us profoundly, who we meet that will forever impact our lives. And isn’t that a good thing, to be surprised by life’s beautiful moments?

We should feel just as inspired by life’s unexpected challenges. When things don’t go as planned – when your new business can’t get off the ground, when you don’t seem to be meeting the right man, or when your MBA gets sidelined by your job transfer to Hong Kong – there is a purpose. These challenges show you that it is okay to let go.

Letting go of expectations and timelines that are beyond our control is liberating. It helps us to stop for a moment, take a look around, and really see what other opportunities life has in store.

Would you rather go through life knowing exactly what to expect, who you’ll meet, and what you will be doing each day? I wouldn’t. The most beautiful moments in my life were the ones that weren’t at all planned, that just happened because I got held up or diverted from my own plan, and ended up doing something else.

I got let go from a job, which led me to three jobs I hated, but also allowed me to meet my dearest friends to this day. I would never have met them had I not been floating from one job to the next, uncertain of what to do. I also wouldn’t have gotten an opportunity to develop my writing skills as I did when I was in-between jobs. I discovered a new love.

Once on a road trip with my boyfriend, we got lost when we missed an exit and ended up in a small town on the Oregon Coast where there were only two small motels. There was also a cyclist convention, and hundreds of people traveling through. It was late at night, and I felt defeated, wondering where we would stay. We were both too tired to continue driving to the next small town, so we took our chances and stopped by one of the motels off the highway. As it turned out, someone had just canceled their beachfront room at the motel across the street, so we not only got to take in a gorgeous moonlit night from our window, but we discovered the sheer beauty of something as simple as getting lost in order to reconnect with each other.

That’s something you can’t plan.

 

Are you dating and having no luck, or have you had a string of bad relationships and can’t figure out what is wrong?

Sometimes it’s difficult to understand why things happen in our lives – why we’re still single, or why we keep meeting the wrong guys. As I say in my book Date Expectations, sometimes it’s our romantic history and patterns that hold the key to understanding why we’re stuck, why we can’t seem to find a happy, healthy relationship.

If you’ve noticed that you keep meeting and dating the same kinds of guys/ girls, or that you don’t find anyone new that you meet particularly exciting, it could be because you haven’t really gotten over your ex. More specifically, you are looking for your ex in all of your future relationships, even if he or she wasn’t so good for you.

Instead of getting stuck in the past, it’s time to really assess what is happening, and how your own dating habits could be contributing to the problem. While you might be meeting the wrong people, there’s a reason you keep meeting them.

Following are some questions to ask yourself to see if you’re really over your ex:

Do you tend to go for the same “type?” Whether it’s physical features, a sense of humor, or someone who shares the same intellectual curiosity, you find yourself attracted to different versions of your ex in every new person you meet. While you might think you have a “type,” – if you’ve dated several guys who were your “type” and yet none of them worked out, you might want to try something else.

Do you find it hard to commit? When we haven’t moved on emotionally, it’s almost impossible to commit to someone new. Maybe you feel pressure at each new relationship, so you tend to keep things casual or delay any meaningful conversation. Consider this: maybe it’s not your date, but that you aren’t quite ready for anything serious. That’s okay. Better to acknowledge your pain and work through it, so you can be ready when the right person does come along.

Is it hard for you to be single? If you’ve gone from one relationship to the next without taking much of a break, then maybe it’s time to give yourself just that – a break! All of us need to get familiar with our own wants, needs, desires – who we really are outside of a relationship. If you don’t, you’ll have a hard time knowing who you are in a relationship, and that leads to a lot of frustration, insecurity, and unhappiness. Instead of jumping into your next relationship, take a step back. Take up a new hobby, join that amateur Dodge Ball league you’ve been considering, or book that vacation to Belize you were going to take with a future partner. There’s no time like the present to get to know yourself better.

Are they or aren’t they?

Or, more importantly, are we or aren’t we?

Relationships have always been a guaranteed source of stress, angst, and all manner of other unsettled feelings, but dating these days is more unstructured than it's ever been and the anguish is even worse in our age of ambiguity.

Whereas once upon a time dating followed a relatively set path, now we're all pretty much running around blindfolded and hoping for the best. From friends with benefits, to long term live-in partners that are anxious about making the leap to marriage, our commitments are fuzzier than they have ever been before. This is especially true for younger generations, who often fear using the terms "relationship" or "dating." “We’re hanging out” is as committed as it gets.

But why this sudden urge to remain ambiguous?

One theory is that those in their 20s and 30s are the first generation to grow up witnessing mass divorce. Having watched their parents split, they may carry a legacy of insecurity with them and avoid intimacy in order to cope with it. They may also simply feel that relationships are too risky a proposition.

On the other hand, the rising incidence of narcissism that researchers are seeing amongst the younger generations may also be to blame. If we are increasingly focused on ourselves, we may also be increasingly likely to reject the responsibility of caring for someone else.

There's also the fear of rejection, which has plagued every generation since the dawn of dating. Throw in online and mobile dating, which allow people to test the waters from behind the safety of a screen, and it's no wonder we feel safer with vague intentions and minimal commitments. The ease of shopping for potential partners via digital means, plus the greater social acceptance of diverse romantic arrangements and the disappearance of clear labels, have all added to the dating confusion.

Initially, ambiguity in such a bad thing, but as a relationship continues, it becomes difficult to navigate. Constant ambiguity comes with certain risks. One person may feel more committed than the other, but may be afraid to bring it up for fear of pushing their partner away. The result is a whole lot of insecurity and time wasted with someone who ultimately isn't seeking the same thing.

That ambiguity is also extending into our breakups. More and more people are having sex with their exes, and far too often one hopes the inconclusivness means the relationship is rekindling while the other just wants a temporary hookup in the interim until they find someone else.

The question now is: will we develop new rules to govern our age of ambiguity? What will they be?

Some of us are perfectly happy to be settled into singlehood. Others absolutely hate it.

The thing is, singlehood can be a conscious choice or an unintentional affliction. If it's the former, rock on and keep doing what you're doing. If it's the latter, sit down because we've got some talking to do. I'm all for people staying single, but I don't want anyone to be forced into singlehood if it's not where they want to be. And here's the hard truth: if you're single and you don't want to be, there's a good chance you're the reason.

Of course you can't control the people around you, and they certainly have a say in whether or not they want to date you, but there are specific, unproductive mindsets and actions you may be responsible for that are keeping you single longer than you want to be.

Are you doing any of these things?

• Not making an effort. Newsflash: if all you do is watch your Netflix queue, you’re never going to meet someone. Join an online dating site. Spend weekends in museums, parks, classes – anywhere you're surrounded by strangers. And don't be afraid to make the first move. If you're not trying in the first place, you can't expect results.
• Dating the same type over and over again. They say insanity is doing the same thing over and over again and expecting different results. That goes for dating, too. If you've got a "type" and it hasn't worked for you yet, it's probably not going to work for you in the future either. It's time to branch out. And the added bonus is that once you've stopped limiting which types of people you will and won't date, the possibilities open up and you have more potential partners than you ever thought possible.
• Choosing partners based solely on a list of qualities. It's a good idea to know what you want and don't want in a relationship, but it can be limiting if you're too attached to your imaginary list. Someone could have every quality on your list and still be wrong for you. On the other hand, someone could be missing most of them and yet mysteriously make you happier than you've ever been. A person is a whole package, not an inventory of dealbreakers. Save the list for Santa.
• Not making space. This is one of the hardest lessons for people to learn. If you want love in your life, you have to make room for it. You can't be focused on your friends, your career, your hobbies, your family, or whatever else is taking up your time, 24/7 if you want to meet someone. Recognize that you're ready to let love in, and leave some space in your life to allow it to happen.

A few years ago, I was at an amusement park with friends when one of them shyly handed me his camera.

“Do you think you could take a few pictures of me today?” Kent asked. “I’m making a profile for an online dating site and I don’t really have any pictures of me. Especially ones that aren’t posed in some way.”

Happy to oblige, I did my best to grab good candid shots of Kent. Everything was quiet for some months, until I ran into him one morning, positively giddy.

“I just had the best first date!” he said excitedly.

“It’s ten in the morning! That must have been some first date!” I said, raising my eyebrows.

“No, no, the date didn’t start last night,” he said, blushing. “It was a breakfast date! She works nights, so this was the fastest way to actually meet in person.”

“Ooh,” I said, intrigued. “So you met her through your dating site?”

“Yep,” he said. “She moved here two years ago and only lives ten minutes away, but thanks to our jobs our chances of running into each other are practically zilch. And since we’re on opposite sleep schedules, it’s been pretty nerve-wracking writing her and then waiting a minimum of eight hours for a response. But still, that’s better than never having met her at all.”

“Well, it’s great that she seems so wonderful, but will you ever get to spend time together with such opposite schedules?”

“She’s going to get moved to a different position at the end of the year,” Kent said. “It won’t be forever. And - this may sound cheesy, but - even if it’s more work finding time to meet, she really seems worth it.”

Last month, Kent and his wonderful first date were married. Her inconvenient schedule was indeed not for forever - but hopefully her romance with Kent will be.

Related Article: Stories in Success, Part I

A few of my closest friends turned 30 this month, and it's got me thinking. There's no denying that dating in your 20s is fun. A lot of fun, if you do it right. But seems to me there's something special about dating in your 30s.

Sure, there are some downsides that come along with it. If you're unattached by the time you reach the big 3-0, you're bound to get comments about how you shouldn't settle but shouldn't get left on the shelf either (how confusing is that?). People ask about your biological clock or if you're afraid of commitment. They tell you that you can't "have it all" or that all the good ones will be taken if you wait. Some might even straight-up say there's something wrong with you.

But on the other hand, there's a lot to love about dating in your 30s, like:

• You know who you are. The 20s are all about finding yourself. You're meant to travel the world, go on crazy adventures, work odd jobs, occasionally squander your cash on silly purchases, etc. some of it will be great, and some of it will be awful. All of it adds up to some seriously important life lessons that you carry with you into the 30s dating game. By then, you're ready to think more seriously about the kind of relationship you actually want and the kind of partner who can give it to you.
• You know what love is. Well, maybe we never really know what love is, but entering our 30s means knowing a whole lot more about it. There's often a very big difference between what you're drawn to, what you want, and what you need. As you get older, you're able to tell the difference and define the kind of love that works for you. And because of that…
• Dating gets serious. In your 30s, relationships tend to move faster. You've been through your fair share of bad dates, inadequate relationships and casual hookups, and you know what you want. If something isn't working out the way you want it to, you have the confidence to end it quickly. And if things are headed in a good direction, you feel equally comfortable pursuing it.
• On the other hand, not everyone wants to get serious. Some people are looking to settle down in their 30s, but others are happy staying single. Both are perfectly viable options that can lead to happy lifetimes. The important question to ask is “Where do I want to be in 5 years? Or 10?” Like it or not, what you do today will have an impact on your relationships in the future. If you do want to be with someone, make sure to create space in your life for it right now.

And most importantly…

• There’s still a lot to learn. Wouldn't life be boring if you'd already learned everything? Luckily, that's never going to happen, least of all in your 30s. Enjoy the weird and wonderful lessons that life will continue to throw your way.