The Lure of a Challenge?

Relationship fails aside, I’ve never had a problem attracting male attention. While I enjoy being pursued, it’s rarely the men who fall all over me that hold my attention. Of course, what I really want is that delicate balance: A man who lets me know he’s interested, but is secure and strong enough he won’t jump through hoops to win me. He’ll put in effort, but he’s not going to fawn or be led around. The balance is difficult to find. What I’ve usually encountered is men who will say or do anything to win me, for whom I begin to lose respect. Or men who think they don’t have to do anything and are apathetic about the relationship.

So, a couple of months ago, I met a guy at a Meetup. He emailed me the day after we met to “extend the hand of friendship” and was very sweet. Since then we’ve kept in touch via text with casual, flirty banter. When I’ve seen him at Meetups, the contact follows this formula: Connect, drift apart to mingle, connect, drift apart to mingle, eventually gravitate toward one another for the duration of the evening. Then he walks me to my car for safety and hugs me goodnight.

Friendly, right? Yet…there’s definitely something beyond friendship there. He makes continual reference to how many people ask me out or give me their number; I have a hard time being able to tell if it’s annoyance or amusement that prompts the preoccupation with whether I’m dating or not. He’s obviously drawn to me. The banter and the eye contact is laden with sexual energy. People continually assume we’re dating. One observer said, “His body language says he’s definitely into you.” Another: “He’s sweet on you.” The people who have asked me out from these groups always ask, “Are you involved with ****?” I’ve made a couple of small hints to him about us getting together, which has been met with…I have no idea what. Not a rejection of the notion, but he hasn’t asked me out.

The last time we were together, I finally, after a couple of hours of following the formula and some heavy flirting, looked at him and said wryly, “You just don’t quite know what to do with me, do you?” With his typical quiet grin, he shook his head and said, “No. No I don’t.” Later on that night he made reference to how we should get together at his house for a wine night, but mentioned that it might be “weird”.

“Why would it be weird?” I ask.

“Well…then you might try to get me drunk and then we’d become friends with benefits.”

“Somehow, I don’t think I’d have to get you drunk.” I joked back with him.

To which he turned and looked into my eyes for several long seconds, before moving onto another topic. He announced at one point that he’d never date someone he met at a Meetup group, because the potential for awkwardness was too high (this was in direct reference to the dates I’ve acquired from Meetups).  At the end of the night he walked me to my car and hugged me goodnight; I kissed him on the cheek. He texted me to say we should do a wine night soon.

Dammit! I’m getting so many mixed signals from him it’s driving me nuts. What drives me even more nuts is the inner acknowledgement that part of my fascination with him might be because I can’t actually tell if he’s interested in me or not. The larger question is: Do I want him to be interested because I’m actually interested? Or do I want him to be interested so that I can win? That is a sad admission on my part, but I’ve had to admit that might be part of it. He’s clearly interested on some level, but won’t do anything about it, which makes him immensely more attractive. The intrigue is…exciting. Which I have typically found does not make a good foundation for relationships, but it certainly is fun!

For now I’m simply letting the chemistry, whatever it may be stemming from, exist between us without trying to force it to be anything. The lure of the challenge is strong, but I’m trying to resist actively pursuing it!

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