Yesterday I got a phone call from one of my close girlfriends in New York. She’s divorced with a young daughter and recently re-entered the dating scene. It’s been six years since she’s dated and times have changed. I’ve experienced some of this myself over the last year, as those of you who follow the blog may recall. There’s all this online dating, okcupid and match and let’s hook up (I may have made that last one up), and texting and tweeting and instagram and seriously, isn’t dating complicated enough without having to distill your thoughts into 140 characters or update your relationship status so everyone knows you’re getting some? Or you were and now you’re not? Or you may be but aren’t sure?

Anyway, she called me because she went on a date with this guy and as far as she could tell it was a home run. They went out to eat and talked for hours, walked through SoHo holding hands and ended the night with a hot make-out session on her couch. He talked about how she’d have to meet different friends of his, and things they’d do together this summer. She felt totally confident they’d be going out again. He texted her when he got home and said he hoped she had sweet dreams and knew he would be. Said he’d call her the next day to make a plan, and that he couldn’t wait to see her again. And then, crickets. It’s been almost two weeks since their date and no contact from the dude. Of course it’s especially crushing because it was her first foray out of the gate, and because she sent him an email a week later “checking in” and heard nothing back. So she wanted to replay the whole night with me to see if she was missing anything because she feels rejected and her feelings are hurt. I got the whole play-by-play in such minute detail, it was as though I was there on the date. She wondered if he’d seen the picture of her ex that she hadn’t put away yet. If it scared the guy off that her ex still works for her dad. If maybe he thought she was conflicted and that she might reunite with her daughter’s father. If she had talked too much about the demise of her marriage even though he expressly asked, and had shared the story of his own divorce. If she had moved too fast by making out with him for so long, or not fast enough because she sent him home without letting him scramble her eggs. You get the drift.

I listened to all of this and when she was done I said I thought it had nothing to do with her. I know her. She’s funny and smart and kind and a total head-turner. She’s confident and sexy, and there’s just no way she’s not hearing from this guy because there’s anything lacking in her. I said all of that, of course, but also just listened because it doesn’t matter if I know all that, it only really matters if she does. I don’t know what’s going on with the guy. Maybe there’s someone else in the picture. Maybe he’s great at first dates. Maybe he got scared. Maybe he likes head games. Who knows? But she’s suffering and watching him update his statuses with pithy remarks and tweet about basketball games and post pictures with friends out to lunch. Of course I told her I thought she should stop “following” him everywhere and get back to the business of being awesome.

It’s incredibly hard to walk away from situations we don’t understand. Especially when it seems that a real connection happened, but we’re not always going to get answers. Some things will be left undone, unsaid, unknown. It won’t all be wrapped up in neat little packages of digestible information. Some people are in incredible pain, in lonely desperation with no idea how to move forward. Some people make a mess of things because that’s where they happen to be when you cross paths with them. Try not to expend too much energy in an effort to figure it all out. Just trust that it won’t be a mystery when it’s right. You won’t be wondering and suffering and having crazy conversations with your friends dissecting every sentence you uttered, searching for the mistake. The hole inside you you must have exposed. The dumb thing you said, or the fact that you snorted when you laughed. You won’t second-guess yourself. When it’s right, you’ll just be happy. (Assuming you were happy already.) Tired, but happy.

Wishing that for you, and so much more,

Ally Hamilton