Dater X: Can Single Peeps And Those In Relationships Just Get Along?

“Dump them both!” exclaimed Sabrina, taking a sip of a gin and tonic before brushing her lush black hair out of her eyes. I’d just told her about the same dilemma I presented you guys with last week—that I was dating two guys and not feeling that into either of them. “Trust me, I know what it’s like to feel blah about guy after guy. And then to get rejected by the few you do feel something for. I did it for years, too,” she continued. “But someday you’re going to stumble into the wrong bar, spill your drink on someone, and your whole life will change.”

I should probably give you a bit of Sabrina’s back story.

Here’s what I have to say to people in relationships when talking to your single friends: Be understanding. Know that while single life is dotted with hot hookups under chandeliers in dimly lit bars, it can also can feel like a game of Hit the Mole where you are the one getting bopped on the head over and over.

Two years ago, she was my wing woman, my favorite single friend to go out with because she was having an equally hard time on the dating scene but always kept a positive attitude about it. One night, she never showed at a friend’s birthday party—very unlike her. I left frantic messages on her cell phone trying to find her. The next day she called to say that she’d gotten drunk at dinner and had accidentally gone to the wrong bar, where, in a tipsy stupor, she spilled her drink all over the guy who was ordering beside her. They started talking and ended up hanging out all night. She’s been with him ever since. They got engaged earlier this year.

“It will happen for you, too,” she assured me.

The next night, I hung out with Linda, another longtime friend whom I’d known in her single days. She fell in love a few years ago with an extraordinary man, and they got married about a year ago. In between bites of her burger, she asked me how dating was going. I gave her the rundown. “How is it possible you’re still single?” she said. “You just need to put yourself out there.”

Now, as Amelia has already discussed, “put yourself out there” are four words that make a single lady’s ears bleed. Because, um, we are. If Linda had been listening to me talk for the previous 15 minutes, she would have heard that I am on two different online dating sites (with these sometimes hilarious results), actively looking through profiles and emailing guys who seem interesting; that I’ve gone on blind dates arranged by everyone from my friends to my rabbi; that I’m currently on two sport teams (softball! volleyball!) to (a) get exercise and (b) meet dudes; that I go to every party/event I’m invited to, just in case; and that, for the next few weeks, for the sake of this column, I’m challenging myself to walk up and make conversation with a guy I find attractive at least once a day. I am out there. Ten steps beyond out there. So out there that sometimes it feels like that dream where you walk into class naked and everyone starts laughing.

And if Linda had been listening to me talk for, oh, the past year, she would have also heard that there have been three guys that I dated, had intense initial connections with, truly adored, and wanted to pursue a relationship with—all of whom broke up with me. I took a few months off to recover and feel so much more hopeful about the prospect of finding love. But still, that hurts.

These two back-to-back conversations got me thinking a lot about how I relate to friends and family members who are in happy relationships. Add on the fact that it is apparently National Unmarried and Single Americans Week—a holiday that seems to imply that single people are a separate species. Sometimes, I think it’s true.

With my single friends, both male and female, there’s a sense of camaraderie. We hang out a lot and share our dating exploits—the good, the bad, and the ugly. There’s a sense that we are fighting our way through the same overgrown jungle together. We have that shared sense of “Oh shit—is that really a two-foot beetle?” and “Wait, did anyone bring a weed whacker?”

But with friends in relationships, they tend to fall into one of two camps: the sympathetic folks who remember the intense ups and downs of being single and the mental jostling that comes from rarely knowing where you stand with people and then there are the ones who’ve either forgotten how hard single life can be or who had a relatively easy time of it. Often, they carry a slight sense of superiority; they seem to think that because they are in a relationship that they’ve figured things out while you must be a bumbling imbecile when it comes to love. They don’t seem to acknowledge that — while being in a relationship absolutely takes skill (communication!) and hard work (to stay on the same page with someone long term!) and patience (to not let the little things about the other person drive you up the wall!)—there is a certain amount of luck involved in finding someone who you want to make it work with and who wants the same with you.

To take things back to Linda, she’s been unemployed for a little while. I know that she is brilliant and talented and that her lack of employment is a matter of circumstance—that she just hasn’t been able to find the right job for her in a tough economy. I, on the other hand, have a high-paying job I love that allows me plenty of writing time on the side. Is this because I am any smarter or more of a hustler than her? Heck no. I know that the fact that I found my job is 50 percent about being really good at what I do and 50 percent the luck of being in the right place at the right time and having the right acquaintance be kind enough to recommend me over the hundreds of other people who are also good at what I do.

I don’t think Linda sees me being single as a matter of circumstance. She seems to believe that I am doing something wrong. And she often brings it up, so that she can point it out. I wish she’d give me the same benefit of the doubt that I give her.

Here’s where the whole dichotomy of sympathetic friends versus the figured-it-all-out ones gets even more complicated: my older sister. My sister had the good fortune to meet an amazing guy in college who loves her beyond belief, and even recently told me that he thinks her road rage is “cute.” They’ve put a lot of effort into making their relationship grow and they got married a few years ago. But my sister sometimes has that air of superiority—telling me I should try to meet someone and berating me for being picky when I break things off with someone I could tell wasn’t my green zebra.

The rift had gotten bad—to the point where I didn’t like to talk to her about dating because I felt she was so not understanding. And then we had a conversation that changed our whole relationship. She was telling me that she bumped into a guy who broke my heart two years back. When we’d been together, my sister kept telling me how she “thought I could do better.” As she told me about seeing him, and that he had a new girlfriend with him, I got emotional. “I know you don’t understand,” I said. “But that’s hard to hear.”

“I understand,” she said, rubbing my back. “Remember Tom?” He was another friend of hers from college. “I was in love with him for years, even though I was very happy with Max. It weighed on me, watching him date my best friend and my roommate. I still get mad thinking about it.”

My sister sharing this made me realize that, even though I didn’t see it, she had struggled in love too. I don’t know why this hadn’t occurred to me before—if there is one thing all human beings have in common is that we’ve all felt love and the black hole that sinks in when it ends or never happens. Ask anyone who’s ever penned a Top 40 single.

So here’s what I have to say to people in relationships when talking to your single friends: Be understanding. Know that while single life is dotted with hot hookups under chandeliers in dimly lit bars, it also can feel like a game of Hit the Mole where you are the one getting bopped on the head over and over. More than that, tell us about your struggles. Share with us your hard dating experiences in the past. Tell us about some of the things you’re having a hard time with in your relationship.

When you’re single, the grass looks greener on the relationship side. And I know when I’ve been in relationships, the grass often looked pretty yummy on the single side. I think if we do a better job of sharing the good and the bad of both sides with each other, we might all be a little happier with our own patch of turf.

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