Pursuing a woman has high stakes.

It seems to me the burning question among single women is, "Why don’t men approach women anymore?" Never mind the cheesy pickup lines; why don’t they just come up to women and say hello. Initiate conversation. Ask the girl for her number. While I think the answer to this question is multifaceted, I will say one of the biggest reasons men don’t approach women is that we don’t want to come across as creepy.

I know for me, "don’t be creepy" is my number one dating goal. Actually, that’s not true. My number one goal is "be assertive," but "don’t be a creep about it" is inextricably linked to that goal. As anybody who has ever tried to build a fire knows, there are two ways to screw it up: (1) by neglecting it or (2) by fanning the flames too hard, too soon. The same logic applies to love. I’m willing to bet the average woman would be surprised to find out just how difficult it can be for a man to toe the line between what they interpret as pursuant (in a good way) and creepy (in a very bad way).

No doubt it's difficult being the woman who has to field all the creepers. But as a guy who is genuinely trying to be assertive and respect women, I’ve had a few experiences in my dating life where I struggled to find that happy medium, and it sucks (I’ve also learned a lot as a result of those experiences, so don't take this as complaining!) For the sake of fostering understanding between the sexes, here’s what it’s like to be a man looking for love and trying to read a woman’s signals.

We Approach with Caution

If there’s one place a woman knows she will come into contact with a creep, it’s at the bar. Women know this, and, believe it or not, men know this, too. Ever wonder why men sometimes don’t seem to have the cajones to approach you at the bar? It’s probably because the last half dozen times they tried, they were given one of those “Get away from me, you creep” looks.

Once I was sitting at the bar with some friends watching the game and minding my own business when I see an attractive woman across the bar who seemed to be giving me the eyes. I didn’t think too much of it, but then she seemed to really be giving me the eyes. My friends noticed, too, so I proceeded into the great unknown.

There was an open seat next to her, so I walked over, introduced myself, sat down, and ordered a drink. About two sentences into our conversation, she turned her back to me and proceeded to ignore me. Since I had ordered a drink, I had to sit there in purgatory until the slow-as-molasses bartender completed my order.

To this day, I still don’t know if she just chickened out when I came over, or if she found out all she needed to know in those first couple of sentences, or if I completely misread her cues. But it certainly made me think twice about approaching a woman at a bar the next time. Was I a creep for attempting? Not from my perspective, of course, but I couldn’t help but wonder how she (and others) perceived it.

The Thrill of the Chase

One time at church, a really beautiful woman caught my eye. Unfortunately, she had made it halfway down the street by the time I got outside the church in the hopes of talking to her. At this point, I had a decision to make: chase her down, or let her go and risk never getting a chance to meet her again.

So, of course, I chased her down. I caught up with her and said, “Excuse me, Miss. I saw you in church and wanted to come over and introduce myself.” She looked like she wasn’t sure what to make of it. I asked her if she wanted to grab a cup of coffee, but she said she was meeting up with friends, and she didn’t give any impression that she was inclined to meet up in the future. I took the hint and said, “Nice to meet you,” and we went our separate ways.

Since then, I’ve relayed that story a few times and have gotten very different sorts of reactions from women, ranging from “Whoa—chased her down? That’s creepy and not OK,” to “Why doesn’t that sort of thing ever happen to me?!” And, to a certain extent, I can understand it. Some women are a lot more comfortable being approached by a random guy, and others not so much. But going out of my way to have a short, pleasant conversation with a woman in broad daylight? It seems to me that scenario could have just as easily become the most romantic meet cute of all time, not a scene from Psycho. Am I wrong, ladies?

Sealed with a Kiss

As Dev found out (twice) in the new season of Master of None, there are few things in dating as treacherous as deciding when to kiss a woman. For my first kiss, I was so nervous I basically asked her to walk me through it. That was rough!

Then there was the time I kissed a girl I was "hanging out" with. We had dated about a month when she wanted to cool it, but we still ended up spending a lot of time together. After a few months, I was pretty sure she was giving me the signals that she wanted more, but I had no idea what I was doing and feared ruining both a current friendship and a potential future romance. We were snuggled up to watch Hitch (aka one of the most romantic movies of all time), and we were just sitting there in the dark after the movie ended. Luckily, she went for it, and we ended up in a long-term relationship.

But there have been other times when I wasn’t so lucky. There was that time I took a friend to a gala dinner event for my work, and she invited me back to her place after I drove her home. Good sign. We ended up playing Scrabble in the candlelight as her roommates slept upstairs, feeling the need to whisper not to wake them. Talk about the most romantic board game of my life. So yeah, I decided to kiss her as I said goodbye. She dodged me and said, as if she were matching the tone from that Jurassic Park guy’s error message, “No no no, Isaac, I need to figure some things out in my life right now.” To this day, I’ve never seen her again, in part because I was so embarrassed. These moments haunt every first kiss and make a guy doubt his ability to identify the green light.

So, how does a man be assertive without being creepy? Unfortunately, there is no one answer. But what I’ve learned through trial and error is that, in some ways, awkwardness is a necessary evil. I will of course continue to strive toward my number one goal: To be assertive in love, but not creepy. But I've resolved to get comfortable with the awkwardness of meeting new people, give other people some room to be less-than-perfect, and be generous in that way with myself, too.

Sound about right?

Photo Credit: Britt Rene Photography