Great Expectations

A little over a year ago, I had a meeting with a 30-something society diarist in an upmarket hotel in one of the leafier parts of Dublin 2. The meeting was arranged on the day of its happening in a text message. “If I were Robert O’Connor I’d be checking the society pages of The Mail today” said the diarist in a sporadic morning text. I was in them, for all the right reasons. I knew instantly that this wasn’t a selfless PR favour, there was an expectation on the diarist’s part. “Meet me for coffee at The Merrion”, the next message read.

I jumped out of bed, threw on yesterdays clothes and power-walked to the local shop to pick up The Mail. There it was, the most complimentary write-up an artist could hope for, but what was the price-tag on this purchase that had been made on my behalf, I wondered. Two hours later, I jumped out of a taxi outside the Merrion, perspiration ruining my Ralph Lauren button-down shirt thanks to the humidity and the lack of AC in the taxi which took an agonising fifteen minutes from the other side of town. I arrived in the outdoor area where afternoon tea was being served. Isn’t this perfect, I thought, good press and great food all in a day, what had I done to deserve such treatment?

The question was what would I have to do, and the answer was, sit back and enjoy the ride, but for someone who is used to driving their own fate, that’s easier said than done. One mini salmon and cream cheese sandwich, two mini cakes and three not so mini glasses of champagne later, I was beginning to entertain the idea of taking the easy way out. “Why make life hard for yourself when someone is willing to set you up so nicely?”, my always straight-to-the-point friend Roisin would later ask me. The fact was, I would have always felt indebted to the diarist, even though there was no financial repayment expected.

A couple of nights later, I waited to be seated in Peploes on the Green, “Robert, you’re in, you’re finally in!”, I told myself. I was in, and two hours later, I was still in, and the diarist was sold on me. Whether it was the idea of finally getting on to the first step in my career or the half-bottle of Domaine du Grand Mayne I had consumed, I was like a real estate agent on steroids, pulling all the right strings until the bill came and the diarist was willing to put their cards on the table, both credit and emotional. Nothing happened that night, and nothing would happen after that night. I’d had a wonderful evening, and everything was perfect, but to me, this was a business deal that was going to cost me an emotional and physical investment I knew I couldn‘t afford.

Several weeks later, following a handful of mostly unintentional and always awkward encounters, I was emptying a watered-down cocktail at a renowned bar on South William Street when I caught sight of the diarist plus their BFF and sidekick, a man who never drank but who always appeared to be wasted, who was in television and who never seemed to know when the cameras had switched off. Conversation with the BFF felt like friendly interrogation and later, the diarist who had recently offered it all on a silver platter, was restrained and yet visibly furious. Had my involvement in two casual meetings suggested I was willing to settle down and become the missing piece in the diarists almost perfect life? A couple of hours later, whilst walking home, I got the answer, “Never contact me again”.

Fast-forward a year and it seems, in matters of love and career, I am not the kind to learn from his mistakes. A late-night Gin-and-Tonic with a London-based business high-flyer seemed to indicate that I was ready to pack my bags and head for Notting Hill. A balanced and charming individual, I just wasn’t in the market for love, but did that mean I couldn’t strike up conversations with people of interest? I figured I could pair the high-flyer with my culture-wealthy friend Gavin, who had been single for some years due to his sensible rejection of half of Dublin as potential life partners. Perhaps I was giving out the wrong message about my status on the relationships market, or perhaps the real mistake was not knowing when to grab hold of an opportunity when one arose. Either way, I was pretty sure I had ended things with my unmentionable termination text message to the well-placed executive.