Darling, people talk about when to go certain places, taking into account things like the weather. For example, one is told to go to Paris in the spring. But what is in Paris in the spring? Parisian women who will be wearing amazing clothes, heels and that French pout. You will look like a toddler in comparison. GO TO PARIS IN THE WINTER. Parisian women will all have red noses and be unable to make charming conversation because their feet are cold. You, in chic but warm boots and a bright red wool coat with matching lipstick, will stop traffic. The museums are empty and the hotels are cheap.
But never visit Paris if you are broken hearted – you will jump in the Seine after seeing attractive couples kissing on every street-corner [the French government gives citizens a tax rebate if you and your petit(e) ami(e) spend one hour per day kissing on street corners to annoy single tourists]. When broken hearted, go to Switzerland. The men, well, shall we say, they look like work in finance, not the finance like “I got money to burn and I want to spend it on buying you Lamborghinis” but “I would like to have a three hour discussion on reverse mortgages.” Your heart is safe in Switzerland, plus it has good chocolate, good wine, lots of cheese-based dishes and good views. You will recover in Switzerland.
In the spring go to North European countries where the denizens will all be sickly pale white or sun burnt. As they (oddly) often choose to wear white clothes and are tall, there is a definite stork-thing going on. Wear flowered shifts and as much pink as possible.
London is slightly tricky. The men look ridiculous – the tight pants/ huge shoes look flatters no one and you will be giggling over your gin. But UK men have good patter, even the most unattractive has got good lines and can be a very plausible fellow. Best to go when you are in a committed relationship so you can enjoy the silly pick-up lines, with no chance of getting stuck in a sunless country with citizens who can’t make a decision without a cup of tea.
Also, never go to London or England if you love British literature. People in British literature are NOTHING like people in Britain, unless you have read only Thomas Hardy.
Places like Amsterdam and Baltimore are safe at all times; there’s enough going on that whatever your mood, you will be fine.
Boston – only in the fall. Never in summer (teeming with parents teaching children to hate American history), never in spring (which occurs on three different days between March and June), never in winter (if you want to be cold, be cold someplace with better food and better views, like Bozeman). And remember, the Puritans never died, they just started wearing khakis. Do not be fooled – this is a city to buy practical shoes in. DO NOT get any kind of beauty treatment, these are people who deep down think that beauty is ungodly. DO NOT go to a spa, DO NOT get your hair cut, DO NOT get a facial, DO NOT get anything waxed. If it’s an emergency, you can go to Lush (Lush stores are always demilitarized zones) and get soap, but if you buy make-up in Boston, DO NOT come running to me that you look like an 18th century spinster whose entire family died in a whaling accident. You deserve it.
New York – go when you are distracted by something else so the city is merely a back-drop. Trying to look at it is like trying to look at the Grand Canyon, you know you are supposed to feel something but after ten minutes of trying to take in the grandeur, you want an ice cream. Treat New York as a setting for something else and it works – you can only understand New York by looking obliquely.
Chicago – go when you need a mood booster. It’s a great place with nice people. They have Frangos and good shopping. And a river. And a lake. Go when you need someplace better than you think it will be. Lots of good food without the pretentions of San Francisco. And no, I am not discussing San Francisco – fog, hills, tech people, I would rather visit Des Moines.