“Why Am I Still Single?”

Welcome to Tough Love. Every other week, we’re answering your questions about dating, breakups, and everything in between. Our advice giver is Blair Braverman, dogsled racer and author of Welcome to the Goddamn Ice Cube. Have a question of your own? Write to us at toughlove@outsidemag.com.


I will attempt to communicate my circumstances and do not mean to sound vain or pretentious, but context is necessary to explain my situation fully, I believe. I feel that I am a person with high morals, a great amount of integrity, and very well educated. I am 25, and I comanage an international real estate brokerage firm in Southern California, pursuing my passions through a career that allows me both freedom and flexibility. I consider myself an outdoorsman and adventurer, and I am very blessed to be able to travel and take time off from my firm to thru-hike some of the most beautiful places the world has to offer. I yearn for the innate beauty that life has to offer, like spending time with my beloved family and friends.

My question is fairly simple. I have many friends who are in happy relationships and seem to be truly experiencing some of the most beautiful things in life. Unfortunately, I have not found anyone who makes me feel this way. I am extremely comfortable being alone and am self-sufficient, but perhaps this keeps me from branching out further and taking risks with girls and love. I believe that I don’t yearn for an intimate connection, because I developed an independent mentality at a young age. (I went away to boarding school when I was 15.) Is this why I haven’t found someone? Is it a matter of complacency or lack of drive, or has the right person just not come along?

As people spend more time with one another, it’s natural that they begin seeing similarities in their mannerisms, characters, interests, etc.; by my understanding, this is how relationships develop. Is it simply a matter of evaluating what my personal interests are (hiking, traveling, backpacking, photography) and then placing myself in the path of success by finding other people with the same interests? If that’s correct, then other people who share similar interests will also be spending their time doing those things, and perhaps we are bound to meet someone we are attracted to.

I tend to overanalyze things, but I am trying to understand. It empowers me and helps me make the best decisions I can in every aspect of my life. I intake information, process and analyze it, then output decisions and move forward. Any advice would be appreciated.

It sounds like you’ve given this a lot of consideration, and it’s nice to see someone approach life, and love, so thoughtfully. You’re a young man who has established himself in his career, takes time to follow his passions, and cares deeply for his friends and family. I understand the thought that love is your next step, that there is surely something you can do to align this part of your life. But that’s what’s tricky about finding love: there’s no formula. We refer to lovers as having “chemistry,” that intangible spark that draws certain people together, but the wonders of science are far more predictable than love. We can work to protect an existing relationship, but we can’t earn a new one, and finding the right person can feel, at moments, like a miracle of circumstance and timing.

Instead, love is a gift we give each other. But there are things you can do to make yourself open to it and be a better steward should that gift arrive. And if you live your life with generosity and kindness, you’re more likely to encounter those things in return.

So let’s talk about how you can make your life more open to the gift of love. Your first decision: Would you rather be proactive or passive about finding a relationship? Neither practice comes with guarantees; it’s just a matter of what’s right for you at this time. It’s wonderful that you’re comfortable with independence, because that will serve you throughout your life, whether you’re in a relationship or not. If you’re happy as you are, you can just decide to sit back and see what happens. But let’s assume, for the sake of this column, that you decide to be proactive.

You’re right that pursuing interests—taking a photography class, say—can be a good way to meet friends and potential dates, as long as the activity is something you enjoy in its own right. If you meet someone, that’s great, and if not, you’ll have improved your photography, a skill that brings you joy and satisfaction. But remember, too, that in relationships, shared interests aren’t as important as shared values—and odds are high that no one in that photography class is looking for a boyfriend. So if you’re serious about trying to find a relationship, I recommend a method with a little less guesswork.

Your friends know you best, and they may have a talent for matchmaking. Let them know that you’re interested in dating and would be open to meeting new people if they have someone in mind. You can also join a singles group (check meetup.com for “singles” and/or “outdoors” in your area) and try online dating, which allows you to say up front what you’re looking for in a relationship and a partner. If your hopes and goals align with someone else’s, and she seems interested in chatting with you, you can ask her out. For first dates, I recommend suggesting an activity (in a public place) rather than taking on the pressure of simply talking over the dinner table. The best way to come up with date ideas is to think of things you’d enjoy doing—then invite someone else along.

You will go on dates that don’t work out, and that’s OK. Nothing is wasted; you’ve had a chance to connect with a cool person, and you both learned a little more about yourselves. Remember that taking the time to wait for the right fit is an accomplishment, not a failure. After all, you’re unique among billions. You’re looking for someone who’s unique in complementary ways.

Finally, one of the greatest ways to open your life to love has nothing to do with dating at all. Try to build and nurture a practice of appreciating people—men and women alike—without expectation of returned sentiments. You already value the innate beauty in life, which is a wonderful trait in and of itself; now try to pay extra attention to the beauty in other people. Notice when someone makes you laugh or tells a story that moves you. Look for kindness in the world and think about how you can add to it. Aim to give three compliments and do five acts of kindness each day, whether it’s leaving an extra-generous tip for your waiter, picking up trash when you pass it on a hike, or helping a friend who’s in a pinch.   

It’s important that you apply these practices to everyone, not just people you might be interested in dating. A woman can tell from a mile away if you’re complimenting her in the hopes that she’ll reciprocate romantically. (Also, unless you’re dating someone, you should be careful about complimenting a woman’s appearance. Since women often deal with unwanted attention, this can feel uncomfortable and even threatening for the recipient.)

If you do these things, if you nurture appreciation and generosity, you’re making the world around you better; you’re building a community that’s kinder and stronger because you’re in it. Does it guarantee you a girlfriend? Nope. But when you’re waiting for a gift from the universe, it helps to give some gifts yourself first.

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