I wave at Penelope as I see her enter my favorite lunch restaurant. I'm a creature of habit and visit the same place for lunch most days—when I'm not too busy to take a break. It's a nice little Italian within walking distance of the firm, so nipping out for a quick lunch date is easy enough usually.

She smiles as she sees me and comes over to sit down at my table. Hanging her jacket over the back of the chair, she pulls a crocheted cat hat off her head and runs her hands through long, brown hair.

"Sorry I'm late," she says with an apologetic smile. "It's my day off and I've been running errands for Amy. The dress shop had misplaced her dress, and we had a moment of panic before they located it."

I fire off one of my more charming smiles. "No worries. I'm glad you made it. So glad we're finally doing this. I wasn't sure you'd call."

Am I imagining a flash of guilt across her face? Surely not. Of course, she always intended to call me. No one says no to the Trevinator.

"Amy pointed out that as the maid of honor and best man we might benefit from being in touch, especially now as we get closer to the big day." She picks up a menu and quickly scans it. "I've never been here. Anything you can recommend?"

"Everything here is amazing."

She laughs. "That's incredibly unhelpful."

"Sorry, I was distracted by looking at you." When her head whips up to stare at me, I fire off another charming smile, wavering a little as she looks a little perturbed. Is she really not into me? Maybe I need a different approach for this one. She might be the type of woman who needs to be a friend before anything else. That's okay. I can do that.

Looking back down at her menu, she stares at it thoughtfully for a moment.

"I hear the salads are great," I say, trying to be a little more helpful.

She smiles, visibly relaxing. Good.

"I'd rather eat something more substantial," she admits. "I can make a salad at home, but I'm rubbish at making pizza. Or these fancy pasta dishes."

I can't remember the last time a date ordered anything that wasn't a salad. Maybe I've been dating the wrong women. We both end up ordering chicken and Parmesan pasta, and I'm relieved when the server takes the menus since I suspect she's been using it as a shield.

"I'm glad you called," I say. "It's been a long time since we ran into each other."

Sipping on her drink, which the server brought around recently, she nods. "I want to say... Amy and Luke's engagement party?"

"Seems about right." I remember little of the engagement party on account of having been plastered for most of it. There's a vague memory of waking up with a blonde the next morning. My life is a combination of work, partying—maybe a little too hard—and women. I like it that way. Seeing Luke about to get married makes me break into a cold sweat. It's not a commitment I'm ready for. Not even close.

"What are you guys doing for the bachelor party?" She looks genuinely interested, and I'm happy to go into details as long as she's looking at me with those big, green eyes.

I can't remember the last time I had a regular conversation with a woman without trying to get her into bed. Not that I don't want to get Penelope into bed, but I've decided I have to hold my horses. She will need more wooing than most, and probably a more gentle approach.

We're halfway through our pasta dishes when I casually ask, "Are you bringing anyone to the wedding?" The question doesn't seem suspicious since we've been discussing wedding related matters for most of the date.

She scrunches her face into a wry little smile. "I only just started dating this guy, and I guess I'm bringing him as long as things go well."

I remember the blond guy she was with at the ice rink. It's a fresh relationship? That's good news for me. My new strategy should be to become her friend, and then I can either wait for them to break up and I will be right there to "comfort" her, or I can try to make a move once she feels comfortable enough around me.

"What about you?" she asks, and I have to think for a second to remember what we were talking about.

"I'm actually bringing my sister," I admit. "She recently got divorced and could do with a fun night away from everything. Mom will watch her kid so she can have a night off."

Penelope's eyes widen slightly, as if surprised. Is it really that surprising that I can be a good guy at times? "That's really nice of you," she says. "I'm sure your sister will appreciate it. Is her daughter the girl I saw you with on the ice?"

I smile fondly. "Molly, yes. She's great. She's my little buddy. I try to take her a couple of weekends a month to give my sister some time off."

"You're a good brother."

"I try to be." I'm surprised by the turn this conversation has taken. I rarely talk much about my family, but it's nice. Penelope seems like someone who genuinely cares as she continues asking questions about my sister and niece. It's a pleasant change to the usual tepid conversations I have on dates, when I always try to keep to neutral topics.

We're in the middle of a discussion about the merits of nieces and nephews—she has a nephew by her sister—compared to having your own children, when my phone rings and I realize I'm late for a meeting. Shit! I can't remember the last time I lost track of time like this.

"I'm really sorry, I have to go." For once, the apology is genuine. I had a great time today. "Do this again?"

"Sure!" She smiles at me and I like it. She has a beautiful smile that lights up her face.

I quickly pay our bill and bend down to give her a friendly kiss on the cheek. That she doesn't pull back, but flashes me another quick smile I take as a win. As I hurry out the door to make it back for my meeting, I can't help but wonder why this date felt different to all the others I've ever had.