Dating dilemma

My boss took me out for lunch on Wednesday, and after a couple of glasses of wine, the subject inevitably turned to men. I am always fascinated by any glimpses I can get into my boss’s marriage, as it is in such a wildly removed sphere to my own experiences and knowledge of relationships. My boss is married to a very successful banker, and their life is a whirl of social events, be it Ascot or children’s birthday parties (both seem to require the same amount of dramatic excessive preparation). Her husband is a perpetual wearer of suits, and the source of a plethora of credit cards. I imagine they have separate ‘dressing rooms’ and certainly have no inkling of each other’s bodily functions. The only potential threat to their relationship that I can fathom comes in the form of their Swedish au pair’s silicone enhanced GG breasts.

These were my boss’s questions about my boyfriend, which seemed pretty innocent, on the surface…
1. How old is he?
2. Where does he work?
3. How much does he earn?
4. How much was his last bonus?
5. Where does he go on holiday?
6. What type of wine does he prefer?
7. What was the last present he bought you?

And my answers…
1. 25
2. He’s a computer programmer, and is in a band
3. No idea
4. Not applicable
5. I think he went to Glastonbury last year?
6. Wine? Pint of lager, maybe a vodka and coke if I’m paying
7. My birthday present I guess – a DVD of his favourite film so we can watch it together.

I thought this was fairly reasonable, but not judging by her reactions…

1. What?! You CANNOT date a younger man darling. At the end of the day, it is all about
that diamond engagement ring, and younger men won’t be as easy to ensnare into
commitment.
2. A band? Oh no, we can’t have him hanging out with young girls at gigs plus there’s no
money in it.
3. Jaw drops.
4. Rapid intake of breath denoting horror.
5. Head in hands
6. Faint moaning sounds.

‘Look’. My boss said. ‘It sounds like he’s very selfish and doesn’t appreciate you at all. You should be admired, chased, spoilt, and preferably by a man who can afford to do it with some style. You obviously don’t go out in the right places, you should be going to bars in the City, Canary Wharf, finding someone to buy you champagne, take you on shopping trips to Dubai…’ I shook my head firmly. ‘No,’ I maintained. ‘I’m just not that kind of girl – I don’t like City types, my boyfriend is creative, and well…thoughtful. ‘How do you know if you’ve never tried?’ she said, wryly. ‘When was the last time he surprised you with something romantic?’ I thought about it. Guaranteed when he had something ‘exciting’ to show me, it would be how he’d come up with improved lyrics for the new Maroon 5 single, or how he’d found a new way to style his hair that disguised that fledgling bald spot. But it was sweet…kind of. Not selfish…was it?

On Thursday my colleague Becca was sent an enormous bunch of stylish flowers by a guy that she had a first date with on Tuesday. The note said to meet him at in a bar in Mayfair on Friday for champagne cocktails. I noticed my wild excitement and disbelief at this gesture was counterbalanced by her own nonchalance. ‘Hmm, Floridita is my favourite place for cocktails, and it’s a bit desperate after a first date, don’t you think?’ she sighed. I was beside myself with shock. The concept of a normal, attractive man I was dating finding out my work address and sending flowers for no other reason than a romantic whim is something of epic movie standards to me. Which was clearly wrong, judging by the knowing glare my boss gave me.

My boss has arranged to take me out to a well known haunt of City types next week, and now, I’m actually quite curious. How would I know what it would be like to date a wealthy man if I’d never experienced it? Perhaps it could be time to do some experimenting…