put myself in the shoes of all those people who decide to buy a watch online, scouring the web for the best and cheapest deal. Be warned: it’s a jungle out there.

1. Scenario: Beset by doubt

While I was strolling around the centre of Geneva I spotted a Tissot T-Touch, and I really liked it. When I got back to my home, out in the sticks, I typed “Tissot T-Touch” into my browser’s search bar. The first site that came up was the official Tissot site, which now has the entire collection available in a new online shop. Thirty-seven different T-Touches were all neatly laid out for me to choose from, with a detailed description of each watch, a spec sheet and a video. They all looked pretty good to me.

I finally settled on a Tissot T-Touch Expert Solar, advertised at CHF 995. But before clicking on the checkout button, I decided to see whether I could find it cheaper elsewhere.

I landed on the website of a major retailer, and found the exact same watch, with the same titanium case, but this time at CHF 1,125! The description was unhelpfully brief, there was no reference number, and in fact I couldn’t even tell if it was the same model or not. Never mind. I retraced my steps and had another go. I visited ricardo.ch (the Swiss equivalent of eBay) and found a brand new watch in its original packaging, with guarantee, for CHF 599. The reference wasn’t quite the same (Reference T091.420.47.057.01) but it looked good, it was also in titanium, had all the same functions and was nearly half the price. But I hesitated. Could I really trust it? Who was the seller? He was offering two other similar models. Was he a retailer trying to move surplus stock? Was this what’s known as the “grey market”? And what about after-sales service? I returned to the official Tissot site, and looked for this new reference number. Yes, it was there, with an official price tag of CHF 995.

I dug deeper, this time searching explicitly for this reference. Amazon was offering it for USD 1,195, with free delivery to Switzerland. I chuckled to myself and moved on. Ebay had one for USD 774.99, also with free delivery. Better, but not better than the one I’d found on ricardo.ch. I persevered, and eventually ended up on Tissot’s US site, which was offering the watch for USD 1,195 which, at the exchange rate on that day, worked out at CHF 1,156, or more than CHF 150 more than the official Swiss price. I scratched my head. Should I keep on looking? Or was I just wasting my time? I got up and went to fetch a beer from the fridge. CHF 599, eBay... It looked like a good deal... should I take the plunge?

2. Scenario: The ignorant millionaire

I’m an extremely busy man. I’m constantly travelling. I have plenty of money, but one of my business associates mentioned to me that the watch I usually wear is a heap of junk. He persuaded me that what I really needed was a proper chunky Swiss watch, the complicated mechanical kind. Not to tell the time, obviously. What I need it for is to show people that I know a thing or two about watches (which I don’t) and that I’m a person of consequence. It’s an important status symbol, he told me. My friend gave me a few brand names to look out for but I can’t remember what they were – they were too complicated. I have a little free time, so I’ll have a look on the internet. I do remember one name my friend mentioned: tourbillon. So I type in: “buy online tourbillon watch”.

3. Scenario: When the Boy Friend catches your eye

I came across it when I was leafing through a magazine. The Boy.Friend by Chanel caught my eye immediately. I’m not particularly into watches, but there’s something about this one that appealed to me straight away. It’s quite discreet but very stylish, and you can wear it day or night. Also, I can’t stand girly watches covered in flowers and butterflies.

I started searching on the internet. I typed in “Chanel Boy Friend” and found myself on the Chanel website. There were 27 models available, from €4,000 to €87,000, although at the top end they had rubies and diamonds. I don’t really need precious stones (I can’t afford them, in any case!) so I went back to the first page. €4,000 is already quite a lot of money. But I deserve to treat myself once in a while!

The first site that comes up is Chrono24. There are 45 pages, and 2306 watches. Good grief. Eye-catching watches – at eye-watering prices. The first one on the page, flagged with a special “TOP” label, is an Audemars Piguet Royal Oak Offshore Tourbillon Chronograph Rose Gold (I told you they were difficult to remember) with a price tag of USD 150,000. A mere bagatelle! But I have to say that it does look the part. I look a little further, and my head starts to spin. There’s a Patek Philippe Grand Complications Minute Repeater for USD 625,000, but it looks pretty plain, and I can’t even tell if it has a tourbillon. There are loads more, some that look like space capsules, some decorated with tiny paintings. I don’t even know where to start. Oh, but here’s one that catches my eye. It’s a Greubel Forsey 97805 GMT Tourbillon 43.5 mm in Rose Gold – on Black Alligator Strap with Anthracite Dial. It costs USD 330,000. You can tell it’s a complicated bit of kit, and I really like the little round planet earth, which I think is supposed to tell the time in all the different time zones. It looks great, it stands out, and it might be useful on my travels. I’ll have a look and see if I can find a similar one, but a bit cheaper. I come across a site called “Gemnation”, which is asking double the price: USD 605,000! But they do throw in delivery and offer to adjust the strap. Which is cool. But wait – does that mean that the other one, the one for USD 330,000, is in fact second-hand? I go back. I was right. According to the seller, EssentialWatches Inc., it is “Certified Preowned” with “box and papers”. And the advert states: “As it is sold as a used watch, in that case you will receive a 1 year warranty. You CAN NOT expect and WILL NOT receive the factory Greubel Forsey warranty on any watch we advertise. We are the sole warrantor of ALL Brands sold on our website.” But that’s still quite a lot of money. Can I trust the site? And if all that complicated mechanical machinery stops working, what am I supposed to do?

I need to talk to my friend. It might be better to try it on before I make up my mind, see what it looks like on my wrist. But... what the hell, life’s too short. I’ll take a punt. My gold card can take it. And, if the worst comes to the worst, I have a good lawyer.

On reading a little further, I realised it was a quartz watch. I think I remember someone telling me that quartz was practical but mechanical was better. A mechanical watch might even be a good investment, I’ve been told. It will keep on working, and I can pass it on to my daughter one day. I looked all through the site but I couldn’t find a mechanical version. Oh well, never mind. But I will see if I can get a better price. After spending a whole afternoon surfing the web, I found one for €3,790 from Fabel GmbH in Berlin, but after adding €76 for delivery it wasn’t really worth it. At that price, I might as well go to a shop and try one on. I looked further and found a whole load more, guaranteed brand new and unworn: €2989 from Prestige Time LLC in the US; €2662 from Jomashop in Brooklyn; €2472 from Tsim Sha Tsui in Kowloon with free delivery...

Could I do any better? I had a look on eBay, but all the Boy.Friend watches appeared to have sold out. Pity. So I typed in “Chanel Boy Friend used” but after a good rummage around I didn’t find a single one. Maybe that’s a good sign? Who knows. So what should I do? Order from Kowloon? I dug a little deeper into this Tsim Sha Tsui. The watch was new and unworn; it came with box and papers, plus two years’ international guarantee. Although they advertised free delivery, in fact delivery to Switzerland cost €98, making a total of €2570. Would I need to pay customs charges on top of that? And what about VAT? I had no clue. Is there anyone I can ask? Well, this evening I’m going to a Chinese restaurant with some friends. Maybe someone there can give me a few pointers...

4. Scenario: Vintage value

I’m young, 22 years old, and I have some friends who are mad about vintage watches. I started to take an interest too, and picked up a few things from looking on the internet, Instagram, and browsing the forums. I’m not an expert by any means, but I do have a few ideas. I decided to buy myself a watch. It had to be a watch with a history: a mechanical watch, a 1970s chrono, for example, in an original colour and with a square case, something cool, a bit of a conversation piece.

I typed “vintage 1970s chronograph” into my search box. The first site to come up was eBay. I immediately spotted a chronograph that had everything I was looking for: shape, colour, everything. Also, it was a Valjoux 7734. I’ve read a lot about Valjoux and it’s all good. But €450 is quite a commitment for me. I was hoping to shell out no more than €200. I took a closer look, to see if it was really worth it. But to my surprise, the watch was unbranded. There was no description. It didn’t smell quite right. My friends had warned me to be careful. You find all sorts of stuff on eBay, some good and some utter rubbish – watches cobbled together from spare parts, fakes, junk movements... I backed off.

But a little further on I found another one, and this time it looked pukka. It was a Lorenz Valjoux 7734 Chronographe Funky 1970s Racing Panda with tachymeter scale, for €268. It had a very detailed description, and the seller was clearly a pro. He called himself “fullywound”, and he was based in Folkestone in Kent. The ad even gave a telephone number, and the buyer had two weeks to send it back if not satisfied. I think this might be the one. But first, I see what I can find out about Lorenz. I go onto the Chronomania forums, and type in Lorenz. It doesn’t take me long to learn that Lorenz’s must-have watch is the Aquastar, and prices are going through the roof. I even find an Aquastar on Hodinkee (that’s a serious website, according to my mates), but the price is €5,000!

Way out of my league. But I’m reassured, and I return to my funky chronograph on eBay. €268!

It’s looking better and better. I should really Skype my friend, who’s an expert on 1970s chronographs, and find out what he thinks. But in the meantime I’ll add it to my Watch List. You never know. I might have sniffed out a bargain, and I’d hate for someone else to beat me to it!