I told you I’d be here for you no matter what! I’m writing this from a distinctly dingy room in Chiang Mai in the north part of Thailand as it buckets rain outside. On Thursday I’ll be flying to Myanmar, where you can bet your ass I’ll still be answering questions for you.

Here’s where to do it – it’s completely anonymous. 

If you start dating a few women at once, at what point does it become cheating?

How long is a piece of string? It’s different for every situation – I mean, someone you only see occasionally but over a long space of time may not expect exclusivity from you, but then again someone you meet twice and have an intense connection with very well might.

A general rule of thumb is to be honest (yet tactful) from the off. You know yourself when something is beginning to solidify as a “thing”. If you feel like you’re being sketchy, you probably are. When in doubt, don’t. Treat other people as you’d like to be treated. All that good stuff. Cliches are cliche for a reason!

My husband is insisting on wearing leggings. At first he was wearing them around the house which I didn’t really mind. Now he is wearing them out in public. I don’t know what to do or say to him. He looks ridiculous.

Usually, my advice would be not to shit where you eat. That said, if you really want to shoot your shot, I think it’s worth figuring out what you envisage yourself getting out of it first so you go into it with your eyes open. If you reckon you’re definitely happy enough to embark on a workplace romance (and all the risk that entails in terms of daily contact and potential awkward breakups etc) then go for it. Just make sure you’ve thought it all through.

In that case, choose a mutual interest – type of food, band, movie, activity, event, whatever – and mention that it’s on and you’re really excited about going. Ask him if he’s going and suggest going together. Then he can tactfully say no if he wants or tag along if he’s into it. Keep it casual. Easy, breezy, beautiful. When you’re both at the thing together, it’ll be much easier for this vibe to progress. 

I’m really envious of your holiday, but can’t shake the feeling that if I tried to do something similar I’d be bored, get quite depressed, and likely bail early and go home. How rational is it to be this daunted by such prospects?

(For those uninitiated in my personal life, which I’m gonna guess is most of you, I quit my day job recently to travel extensively in South East Asia, hence the basis for this question.)

I was getting a blood test a few weeks before heading off and the doctor asked me how I felt about going. I said, “Nervous and scared, but that’s normal right?” She replied, “It wouldn’t be normal if you didn’t feel that way.” And as for going home early? The last thing my mother said to me was a firm: “Come home if you’re not happy.” It’s okay to feel daunted and it’s okay to try and see, then find it’s not for you. Those are all normal concerns.

The way I look at things that states of being are generally comfortable, but it’s the transition between them that is often challenging. And lookit, we’re all different. For some people, the type of travel I am doing – moving rapidly between cities and countries in a relatively short space of time – would be a nightmare. Others thrive on it. It’s easy to say you don’t know before you try, but there’s truth in that. It’s good to confound your expectations and test out if how you see yourself and the world has any basis in reality every once in a while. Travel is good for that, but so are plenty of other things. Trying new things is absolutely vital, I believe, but that doesn’t have to be something as major as what I’m doing.

I’m surprised you link boredom with the experience of a new culture. Why is that? Have a think. Why do you see yourself this way? 

Fifi, what should I do with pictures that I had taken with my ex? Keeping them all in a big folder on my computer feels weird because it was a pretty toxic relationship, but I feel like I’ll regret erasing memories of two years of my life.

Put them on an external harddrive and put that in a shoebox in your room. Delete the folder then. Consider it like a digital memory box, like how you might have kept cinema ticket stubs and cards in the past. Put it in the attic of your mind. You’ll probably be ready to chuck that harddrive in a few years.  

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Confess a story, ask for help or just shout into the void for a bit and see if that helps. All welcome. Anonymity totally guaranteed always.