• Tiffany Philippou

Dear Tiff: How do I rebuild my social life after a break up?

Updated: Nov 15, 2021

I'm missing the sort of friends who feel like family. The weekends feel lonelier for sure.


This article was originally posted in my newsletter - the Tiff Weekly.



Dear Tiff,


My boyfriend and I broke up recently. This is not about him but about the realisation that the break up has led me to have about my social life.

I'm a sociable person and not short of friends, but what I do feel short of, is having a close-knit circle of people I could see on a Fri/Sat night at short notice or just hang out at each other's homes for example. The sort of friends who feel like family. The weekends feel lonelier for sure.


With my ex and ones before I've often integrated into their friendship groups so my weekend plans were largely taken care of. Either we'd hang out together or we would see his friends etc. Now that I'm single again (I have been largely single for the last ten years) this time around it feels worse I think for a few reasons:

Firstly because I now work for myself. This means I don't have colleagues or built-in social events through work like I did before. Also because my work keeps me busy I don't enjoy day drinking or late nights in the week as much; I need a lot of rest to feel energised and productive for my business. Secondly, coming off the back of the pandemic has meant some old friends have moved away or we've lost contact, and last, I'm now at an age where people are settled with partners/kids. They will be more insular with each other than when we were younger and would socialise more together.


I feel ashamed to say that after living in London for 8 years I could still do with a stronger social group, and whilst I'm happy that I've collected lots of friends over the years there is not a default 'group' left other than some girls from school but we're all spread across the country.


My question is how to build new or strengthen existing friendships so that I feel like I have options when it comes to hang outs at weekends etc. I'd love to have more local friends nearby, as well as those in similar work situations, and without partners.


I am also considering this as an opportunity to travel/live abroad briefly as that's on my mind. With a flexible career and no ties it could be a good time.

Ultimately I want to meet Mr Right and build a life together and all that soppy stuff, but until then, I feel that focusing on building my life and friendships should take priority and I'd love your help thinking this through!


Thank you, Social Friend




Dear Social Friend,


Breakups are tough as they force us to re-evaluate our lives and ask ourselves how we want to fill the space that a partner has left behind. This stuff is hard and I salute you for knowing what you want. You’re seeking the friends who are like family, the spontaneous group hangs and the Saturday nights chatting on the sofa over Strictly with wine glass in hand. You want an ease and depth to your social life that’s so brutally robbed from us as we grow older. As we transition from our twenties and into our thirties, our friends are no longer as available to us and I’m beginning to think the greatest pain of growing up is the impact it has on our friendships.


What you want from your friendships is possible, but it’s going to take a lot of time and a lot of work from you. Groups, especially ones who themselves are bonded by history are nearly impossible to penetrate unless you date a member and so my recommendation is to rather than seek to slot into a group, see the question – how do I create my own?


You are right to want weekend friends. I got tired of those pals who you arrange to meet in five weeks time on a Tuesday night long ago. Weekends are premium social time and you’re a premium person and you need to find people who match your availability and appreciate your value to offer you a premium slot in their social calendar. However, with all these wants, it’s going to take some time. Think of it like dating, there’s a whole courtship that happens before you get to a stage where you meet up at short notice or do nothing together at each other’s houses. In the early days, you’ll have to make plans, go out on dates with your new friends and give over some of your weeknights.


The good news is, you’re seeking people who are likely to be available and have time for you and who will likely be going through something similar. They’ll also be more available on Friday and Saturday nights than we were in our twenties because party invites are fewer and far between as we age (for me anyway).


You talked about being ashamed, but don’t be. I believe we’re always evolving and changing and our friendships reflect that. I also believe that we should always be seeking and making new friends and looking to deepen the connections we have. Our society doesn’t place enough importance on friendship and sadly so many people feel like there’s something wrong with them if they just ‘don’t have’ lots of friends. May I add, having a fulfilled social life is one of the best things you can do for your future relationship and I warn you against seeing your new social life as a temporary solution while you wait for Mr Right to slot in. You are about to embark on a journey to rebuild and redesign a social life of your choosing. It’s both scary and exciting.


But let’s get onto the main question - how do I build new or strengthen friendships?

You say that you’re sociable and the fact that you care about this and want to do something about it leads me to believe you have the raw ingredients to befriend people. I’m going to presume that you meet and come across people (as a side note, friends of friends are a great source) and so the ‘top of the funnel’ isn’t the problem here – it’s how to strengthen and build on those friendships with people you come across who you have an inkling could be your sofa-chilling buddy (one day).


Brace yourself, it’s going to require bravery and far more so than dating. To reach out to potential friends is going to require levels of vulnerability that perhaps you weren’t even aware of. ‘Do they hate me?’ ‘Am I cool enough for them?’ ‘Do they want to be my friend?’ All these thoughts are part of the process – you have been warned, but don’t let that hold you back (FYI they’re probably thinking all these things too.)


The recipe is fairly simple – be someone people want to hang out with, reach out to people and start inviting people to stuff – but how?


In the early days, you’re going to have to be very proactive, but very cool about it. We run the risk of being a little too intense with new friendships and whatever you do, don’t love bomb a person – we’re looking for long-lasting sustainable friendships over here, so be measured in your approach.


Flirt a bit on social media, say it was nice to meet them, respond to the occasional post, engage with their content, be interested in them. Create your own content for them to respond to. Test the waters, see if and how they’re responding to you. Find points of shared interest and connection and foster them. Send relevant links related to their interests, invite them to an event that might be a talk on something you’ve discussed or to a gym class they mentioned they’d like to try. Maybe buy a couple of tickets to a show and ask if they want to come with you because you just have ‘a spare ticket’.


But then I repeat. Be cool about it.


Don’t put all your eggs in one basket, you must pursue multiple friends at a time. You are building a network of like-minded mates, not finding ‘the one’. It’ll take the pressure off your interactions and this approach accepts that some of these friendships may be short-lived as their lives change, and that’s ok.


If it feels one-sided, then peace out – this person is not for you. It’s not personal, they may just not be as available as you. I assure you there are plenty of people near you who are available, it’s just a matter of finding them, feeling it out and forging a connection. But if your investment is being matched then slowly and steadily, build on that.


Perhaps after your first event together, or when you see them IRL at another event, you can upgrade your new friends from social DMs to WhatsApp messages. When it feels right, ask them to just hang out if they fancy a drink rather than there having to be a shared interest event to go to.


Start sending voice notes. See how they respond to each of these moments as you move through the friendship stages. Are they matching you? If you both can’t wait for the new series of a TV show, say – why don’t we watch it together?


Become someone who hosts and do it often. Inviting people round when you’ll be home anyway is a very chill way to level up the friendship. And then comes the real how – get vulnerable with your new friends asap. There’s a freedom to be found in discussing stuff with your newer friends and people who are in the same life stage as you. So be open, they will likely be in the same situation as you and there you’ll find your bond. The art of making new friends is knowing how and when to move from being very cool to very uncool. Be uncool when it comes to opening to them and sharing yourself with them. It’s the most likeable thing you can do.


As you deepen friendships, you can start building a group (or perhaps a few different ones with differing shared interests?) Throw a party, invite acquaintances, introduce your friends to each other – become someone who people can meet other people through. If you become the one people see as the one who brings people together, then people will start coming to you.


You mentioned moving abroad and I say why not? But in the context of making friends, the only difference if you go abroad is that you’ll be forced to do it and so you’ll have to be very proactive and being proactive is what I’m advising you to do here. Be proactive and be patient and before you know it, you’ll have formed those close-knit ties you’re seeking. It may look and feel different from our hangs of our twenties, but it’ll be a lot more fulfilling.


With love,

Tiffany