This week in the Men Are Not Perfect series, which you can read in full here, I’ll discuss my experience in having a serious relationship with a woman with a child. For the record, I don’t consider a woman having less than three kids a “deal breaker.” I like to think I handled this particular relationship as best as one can for any serious relationship that doesn’t end in marriage. Still, with the clarity of hindsight, I realize there are a number of areas I should have managed better as a man and arguably as a person.

My friends and I were out having a good time and enjoying the nightlife at a familiar lounge. We had just decided to move to another happening spot up the street as soon as everyone finished their latest round of drinks. The night was young. I was sitting at the bar waiting on one of our friends to return from the back of the club. That’s when I saw her at the door.

As she fumbled in her purse looking for her ID I soaked her in. She had on knee-high black leather boots – many women’s favorite accessory and a personal weakness of mine. I took a swig of beer to calm my nerves. She was at a distance, but with the help of her boots, she looked to be around 5’8. She had long black hair and a form-fitting dress that accentuated the curves of her hips. Those hips! I could already tell from the front there was greatness in the back.

She was fine. Too fine. Like the kind of fine I definitely wouldn’t randomly approach. Besides, I didn’t have enough liquid courage in my system, yet. I decided it was too early in the night to get turned down. Not to mention I didn’t have my boys to act as a support system. It had only been a couple of minutes since I first laid eyes on her, but I had already decided she was out of my league. “She probably stuck up or got a man or something,” I convinced myself instead of accepting that I had punked out.

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The front part of the lounge was a small one-way entrance. She was going to have to pass right in front of me by less than a few feet. Since I didn’t think anything was going to come of it, I didn’t try to hide the fact that I was staring. She was laughing with her friend as they walked towards me. I might as well have been a bar fixture the way they ignored me, but then she let her guard down. It couldn’t have been more than a second, but I distinctly remember her looking me right in the eyes as she passed by. I was in shock.

For the record, this would later become a repeated debate of great contention whenever we retold the story of how we met. In my head, she looked me dead in my optic stems, licked her lips, and made the ‘come hither’ face (granted I was almost through my first beer at this point, so who really knows). Her version, admittedly more feasible, says that she had bad eyesight, which she does, and she wasn’t wearing her eyeglasses that night because “they make her look stupid.” Half-blind but still trying to look cute, she squinted in my direction for a brief second, ALLEGEDLY never licking her lips, and smiled because she thought she recognized me from high school. Regardless of who stared at who or what for how long and why, it was enough for me to go on. I WAS HYPE!

As she passed to my right, my friend finally returned. “Let’s bounce.” “Uh-huh,” was all I could manage as I ignored him walking in the opposite direction of my latest crush. I saw my friends collecting outside as they stared back at me trying to figure out why I wasn’t moving. Unknown to them, I was trying to figure out if I should leave or approach the woman who had (in my head) just stared me down.

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In a rare rule-breaking moment for me, I chose to give chase.

I veered away from my friends and fought my way deeper into the belly of the lounge. A few polite shoves, elbows, and Michael Phelps arm-swimming techniques later I was in the middle of the club looking for a devil in a blue dress with black boots. I spotted her standing at the bar with fresh drinks that I wasn’t sure had been purchased by her or any number of the potential suitors standing in her general area. I didn’t care. I did my best to gain my composure and approached the bar.

“Hello,” I said to the back of my enchantress’ head. I couldn’t see her face, but her friend was facing me. I’d seen this game unfold a number of times over the years. The girl-friend gives non-verbal approval or disapproval to their friend before she even turns to look at you. Her friend made eye contact with me, then with her, and slowly grinned over the straw perched between her lips. I took this to me mean I had the green light.

My potential love interest finally turned around, paused briefly to look me up and down, and then smiled herself. I couldn’t tell if she remembered me from earlier. A “Hey?” escaped her glossy lips. I wanted to kiss her right then and there.

I hadn’t thought this through. ‘Hello’ was actually the beginning and end of all the game I had, but I realized she was waiting for me to say more. “Hey…ummm…yeahh…uhhh…Hello… I don’t mean to be rude to you and your friend,” I was starting to gain some level of composure and think in complete sentences again. Tell her your name, fool!

“My name’s [WisdomIsMisery]. I saw you when you came in and ummm uhhhh, but my friends and I are about to leave. I was hoping I could get your number? Maybe uhhh, talk to you outside the club sometime?” Who the hell do you think you are man, Alicia Keys?! I was blowing it.

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“Is that all?” she laughed. “You don’t even know my name or anything about me….You’re not even going to offer to buy us drinks or anything? You’re just going to get my number and bounce?”

I was ill-prepared for a game of 21 Questions and it seemed like I was getting dissed. Normally composed, the beer or her presence was increasing my intoxication. “Nah, see, look…my friends and I really are leaving. Plus you already have drinks! (she laughed). But I’d love to get to know you better. What would you like to know about me?”

She peppered me with light-hearted questions. I answered some and laughed away others. I wasn’t sure how much time had passed, but suddenly I felt the pressure of a hand on my right shoulder. I figured her boyfriend had finally showed up and a fight was about to ensue. I spun around expecting the worst only to find one of my friends standing there confused. “What the hell are you doing?!”

“I’m talking to [name redacted],” I gestured emphatically with my head towards the curvaceous woman to my left while saying Get Lost with my eyes. My friend was undaunted.

“OoooooooOOOOOOOOOoooooooooh, well excuse me!” He had obviously partaken in a few shots during his absence. I used this as a justifiable reason to bring my conversation to a close. “I told you my friends were waiting on me.”

She laughed. “I see… Fine. You can have my number [WisdomIsMisery].” She seemed apprehensive. As I went to pull out my phone, she stopped me and her demeanor was noticeably more serious. “I should tell you now… I do have a son…Do you have any kids?”

“That’s fine. I do not.”

“Ok,” she said as she put her number in my phone. “Call me…”