Summary: Though not what she'd hoped for, Angela's first official date with Tony evokes a myriad of feelings.

The anticipation, the excitement, the fun, the hope – and finally, the disaster and disappointment. I've had some bad first dates – okay, some dreadful first dates – but I never dreamed that a night out with Tony could end so miserably. And those few hours when I thought he'd asked me out because of pity were among the most heartbreaking of my life. The tears that wanted so desperately to fall sorely tested my stubborn resolve to withhold their descent. To further add to my humiliation, I let that obnoxious comedian snap my precarious control, demonstrating to everyone, including Tony, how deeply hurt I was by his motivation for the evening.

Even now, knowing, or more aptly, trusting that my paid escort was merely a catalyst for what Tony insisted was a sincere invitation, isn't entirely enough to assuage my self-doubt. And I hate that. I want to believe in my own attraction and be confident in my instincts and emotions about Tony. But I'm not, and judging by my behavior tonight, despite my desire to the contrary, I have to wonder if I'll ever be ready to accept Tony as more than my friend.

Although my deeper feelings were stirred by his admission that he thinks I'm beautiful (twice), those emotions were once again returned to the recesses of my heart, replaced with the comfort of friendship by which we've come to define our relationship. Despite my success – and often contentment – in forgetting that my feelings for him have delved into the tempting and dangerous river of love, there are still moments, such as this evening, when I hope that we're not condemned to a lifetime of treading in the safer pools of friendship. I want to believe we are – to keep the metaphor going – swimming slowly toward something more. How can we be so much a part of each other's lives and still pretend that we're looking for a relationship with other people. I can't, and my instincts tell me he can't either. But neither can we yet break from the security in which our relationship so comfortably rests.

Perhaps tonight, with all it lacked, served a higher purpose. I was certainly caught unawares when he so casually invited me out while cleaning the breakfast dishes. Most women are extended such an invitation via a phone call or a note attached to a bouquet of roses. Few, I'm sure, are asked out in their own kitchen, dressed in a sweaty jogging suit, yet not even slightly self-conscious in front of the person doing the asking because it's her best friend.

I can't think of one man besides Tony with whom I've attended a banquet, ceremony, business dinner, social event or even a movie since 1986. Hence, the only reason I had to be surprised was because Tony was asking for no apparent reason. As he so aptly pointed out, all of our previous "dates" were for business or under some other circumstance that did not require intent or planning on our part. But once it became an official date and not simply a night out or a shared dinner, the potential was clear, and so were the questions, namely, what could this mean and why now? After five years, Tony and I were going on a date.

Suddenly, my wardrobe was inadequate, my hair was uncooperative, my make-up unflattering, and my nerves unsteady. And with my limited perception, I'd hazard to say Tony was a victim of similar insecurities. Why else would the same man with whom I've dined on gourmet meals, drank exquisite wines, and danced in seamless harmony choose a bawdy comedy club for such a special occasion?

With the night behind me, I can say now that I'm glad it happened. It was such a pleasure to go on a date, and call it a date. Though once we were out of the house, it hardly felt like a first date. Can there really be such thing as a first date among two people who've lived together for five years and practically share two children? There have been so many dinners and times shared in which we've exchanged stories of our lives and pieces of our selves. Still, I never dreamed Tony had retained so many small details of my life. The feelings such attentiveness evokes are both endearing and provocative, though as always, also silent.

But the true pinnacle of the evening came when we were home, the hurt feelings behind us, sitting together as the Marx Brothers brought mutual smiles to our faces. No pressure, no expectations, no fear. Just two friends sharing timeless humor with no greater pleasure than each other's company. Such an evening has no rival.