I once told a guy, “You love love.” What he later told me I meant was, “You’re more thoughtful than most guys I meet. I secretly love that.”

He’s right; I admit it. I’m guilty of not always saying what I mean. I’m only human, right? We all have our reasons, our own little code language. Maybe it just takes meeting the right person to see that those barriers are there to be broken through, that the right person will properly translate what we’re trying to say.

So I knew this guy was different from the first night we went out. He asked me more personal questions than any guy before him had, and I felt comfortable answering them. What’s more? He asked me questions I didn’t have answers to, ones that made me stumble and hesitate, and thus far, that hadn’t happened with other guys either. He also thought he had the answer to my  every problem, like when I told him I couldn’t hang out because I needed to write this column. His solution? He told me that he also had work to do, so he would bring his laptop over to “work alongside me.” (Come on—ff that’s not code language, I don’t know what is.)

When I told him, "You love love," I wasn’t wrong, nor was I lying. He's wanted a girlfriend since the moment I met him, obvious with each grandiose romantic gesture he made—ones I didn’t know existed outside of romantic comedies. But there’s more. My nature is to push a guy’s buttons, to be sarcastic and make light of situations. If I had said, “You’re so thoughtful,” or, “I love when you do that,” then I would be opening myself up to him and by proxy, subconsciously or not, the possibility of either a relationship or rejection. Maybe I just don’t know if I’m ready for either.

***

A few weeks ago a close friend of mine told me he needed my help. I knew it was serious because he agreed to meet me right outside my office at five after noon, the exact moment the clock strikes freedom for me each day. He had a glow about him that I recognized all too well— you know it too—that something special happened last night kind of glow. It falls somewhere between, “I just spent a few hours in the sun” and “I just left the best workout class ever,” and there’s no one that doesn’t wear this look well.

I had helped him with what to text this girl before, so I allowed myself to bask in the glory of their fantastic date at the Yankees game. I was proud of him for buying really good seats and excited to hear that they made out a little bit in the car service on the way home. As we walked, he told me how she talked about hanging out again: going out for dinner, something before she went away for July 4th, or meeting him in a few weeks because they'd both be in the Hamptons then. As we sat down at a table across the street from my apartment, he showed me pictures of her on Facebook and I was really excited for him. She was just as gorgeous as he built her up to be.

On any date checklist, it seemed that we could mark off every box. But now it was time to turn last night into a next date. We sat in the sun, passing his iPhone back and forth, editing, until we arrived at the perfect next day text. We agreed that he would send it later that afternoon—not too early, not too late. Satsified, I went home for a nap.

One week later he got a text from her. Here's what he told me: Bottom line, she had fun but doesn't think we have much in common. She doesn't want to lead me on so it’s best we don’t hang again.

My heart broke for him. He was so confused by the fact that she initiated the hooking up on the ride home and the talk of hanging out again, and then this. Why would a girl kiss a guy if she wasn’t interested? Why bring up hanging out again if she knows she doesn’t want to? I all of a sudden felt bad about any guy I had kissed then later told we weren’t right for each other. So why do we do this? Are we women mean, horrible creatures? The short answer is: Sometimes there is no good explanation. We get caught up in a fun moment and say things that at the time feel right. But it’s not just us; men are just as guilty of this fickle behavior. Nearly all of us have been on both sides of this equation and can agree that, especially when alcohol is a factor, there’s a lot more at play here.

***

What I’ve learned in dealing with men—and of course there’s no hard and fast rules—is that if he likes you, he’ll call you and make plans to see you. It’s just that simple. I’d like to say it’s the same for women, but I just don’t think we’re as black and white. The bad news is: I’m not sure it ever ends. It’s a lot like the whole "Do I look fat?" thing. We say we want you to tell us, but really, we don’t.

Then, of course, there’s flirting. It’s complicated because every text, tweet, or tag can be construed in so many different ways. I know when I’m flirting with a guy; the problems arise when he thinks I am when I’m not, or when he misinterprets my flirting for something more substantial. Sometimes, we flirt because we can. Other times, we flirt as a sort of push and pull to gauge a guy’s feelings. We also might send contradictory signals because our body is saying one thing while our heart is saying another.

***

I was always taught to say what you mean and mean what you say, but sometimes against better teachings and judgment, it’s just not that easy. The other day I told one of my Mom’s best friends the story of my friend and the girl from the Yankees game. I said maybe she kissed him because she had too much to drink. She said maybe she kissed him because it was easier than talking to him.

I love Sharon because she always says what she means.

Next Week: Jamie shares her thoughts on the complicated balance of working and dating.