I always get so many questions about how to break the ice when it comes to dating. Not only dating actually, in everyday social situations too. As someone who is a) shy and b) mostly an introvert, this type of communication skill is something that I’ve had to learn over time and completely understand the anxiety that can come along with the challenge of not knowing what to say!
Ok, so dating. First of all, let yourself off the hook if you’re stressing out about not knowing what to say! In dating scenarios, it’s a given that there is likely to be an air of awkwardness and both people will be experiencing some kind of nerves. So don’t feel you have to be the one entertaining your date with your wit, charm and sophisticated choice of conversation! Ultimately, a date is 2 people getting to know each other.
Before you even go on dates, you want to be thinking about what defines you as a person. What are you bringing to the table when it comes to meeting someone for the first time? What do you want to share about yourself? What are your hobbies, interests, passions, favourite places you’ve travelled, your goals? These are all really good talking points to turn to throughout the date, and topics you can also ask your date about.
Humour is also a very effective way to break the ice, and as long as it isn’t offensive (!), it will immediately put the person you’re with at ease. Laughing is the best way to banish any sense of awkwardness. The key with this though is to not try too hard to be funny as that will have the er…opposite effect! Just be natural.
If you really don’t know what to say, just call it out! Tell your date you’re a little nervous and that you find the situation a touch awkward. The key to getting this right is to do it with some confidence. You don’t want your date thinking you’re going to completely fall to pieces, but more that you’re just ok with admitting you’re nervous. This is why it’s so important that, when you commit to dating, you have a really solid sense of self and you can fuse your vulnerabilities (which we all have!) with confidence. That is an instant connector.
Something fun you could also do is have a list of 3 unusual questions that might initially sound quite random, but will get your date to reveal more about their personality immediately. Some examples include ‘Have you ever met one of your heroes in person?’ ‘What film character are you most like?’ etc and get your date to ask you 3 more questions too. This then completely shakes up the ‘interview’ style date, which can be repetitive and a huge buzzkill!
Another tip is to go armed with a few stories about yourself that you can work into the conversation. Stories that are funny, engaging or have meaning are the most effective. Examples could be a monumental travel experience, something unusual/funny that happened to you recently or something you did/saw that was out of the ordinary or created an impact on you. Stories you’ve shared before that have received a good response will be handy ones to keep in mind!
Finally, when it comes to dating and social situations, we completely underestimate how important listening is in breaking the ice. We often feel that to be interesting, we have to be the one talking and ‘entertaining’. When you properly listen to what people are telling you in conversation, you’ll ask less surface style questions, and they will notice this! People who have mastered the art of listening are regarded as more charismatic, and instantly make others feel far more comfortable and special in their presence.
To bust right through first date awkwardness, I’ve helped out Match on their upcoming Datemaster Bus campaign, which sounds like SO much fun. Over 3 days the Datemaster Bus offer singles a place to speed date on their way to work. The idea is to give single Londoners, who may otherwise feel too busy to meet new people, the opportunity to date during their morning commute.
The bus departs from different location across London and terminates in central London, ensuring you make your 9.30am meeting.
I’ve provided a few tips and icebreaker questions for the Datemaster Bus, so I’m excited to hear what feedback the event gets 🙂 I think this is such a great idea as firstly, it’s a really fun twist on speed dating and also it’s not in a bar situation where we can so often rely on alcohol to create connection. You’re seeing people in the true light of day and I think it will offer the people taking a part a far more realistic picture of the people they meet. The games Match have put together are designed to be fun but also create connections in a short space of time.
If you’re in London, single and keen to get involved, you can sign up here https://uk.match.com/pages/advice/datemaster/.
It sounds like huge fun and I think it will be a really interesting dating experiment!
This is a sponsored post

One of the most frustrating things about dating websites and apps is that with the masses of people on them, it’s become very hard to go from matching/liking/talking to getting on an actual date. You know, getting in front of a real life human. You can be ‘talking’ to multiple people, many of whom can suddenly drop off the radar, which makes the nature of the the whole thing somewhat disposable. And often annoying if you’re seriously looking to meet someone.
A really innovative and fun development in the dating space to try and combat this has happened and I’m so excited to be a part of it. Dating site and app My Mate Your Date has launched a matchmaking service whereby members can call on the experience and expertise of a panel of Dating Concierges (me being one!) to find and arrange suitable dates for members.
Over 15,000 Londoners have joined My Mate Your Date so far, and at 5pm each day, are presented with a handful of single prospects who are within their social circles. The Dating Concierge service now allows members to book the services of a relationship/dating professional to find and fully arrange three dates within 30 days (it’s only available on iPhone at the moment).
The founder of My Mate Your Date Dan Joyce was inspired to start this new service due to feedback from members and has said that “So many of our users report becoming disillusioned with the online dating market – so many matches, so few meaningful chats, hardly any quality dates. We’re looking to change that with our Dating Concierge service, by getting people offline and on to good dates as quickly as possible.”
How it works is that you firstly arrange a free phone consultation with one of the matchmakers. Then, if you want to go ahead, the matchmaker will meet with you in person or via Skype video to discuss your relationship goals, tastes and values. From there, we’ll search the database of members to find suitable matches based on everything you have told us and set you up on 3 dates in 30 days. We even arrange the date, which will be an activity, dinner and/or drink. Hopefully, you’ll then hit it off with one of those matches…..and who knows what could blossom from there!
The service costs £300 and we’ll get you on 3 dates in 30 days. So, if you fancy being set up by me or one of the other dating concierges, get yourself signed up and the app downloaded here pronto!

If you’re anything like me and just a little bit obsessed over Millionaire Matchmaker and fancy yourself as the next Patti Stanger, I have something very exciting to tell you about.
Britain’s top Matchmaker (yes – she has the awards to prove it!) Caroline Brealey has set up the country’s first Matchmaker Academy to teach wannabe cupids the tricks of the trade.
This bespoke Matchmaker Training weekend will be held in London at the super swanky Fox Club on June 13th and 14th and aims to help participants become successful matchmakers by giving them the tools and knowledge needed to make it as a real life Hitch.
I’ve seen first hand how dedicated to her craft Caroline is - she really knows her stuff when it comes to the love business. It’s no surprise she’s officially the UK’s and the world’s best matchmaker as well as the head judge at this year’s UK Dating Awards. So you’ll be in the best hands!
Caroline said: “Since setting up my own matchmaking agency, Mutual Attraction, over three years ago I’ve learnt first-hand how to run a successful dating business.
“Matchmaking is a fantastic career and you have the freedom and flexibility to shape it exactly how you want. Matchmakers work part time, full time, locally or internationally. From their own home or offices. Some operate on a freelance individual basis whilst others run big agencies. Aside from a job, matchmaking is a lifestyle choice.
“People pay several thousands of pounds for a matchmaker and they want a trained professional who will take care of the serious business of finding them love.”
The academy and the certification is going to set the benchmark for all matchmakers in the UK, improving standards right across the industry.
Guest Speakers
I’m going to be speaking at the academy, sharing my insights on how valuable coaching can be within your matchmaking business and as an additional paid service. The other speakers and dating industry experts are -:
Katy Horwood
Katy writes the award winning dating blog ‘all sweetness and life’ and is a dating columnist for Metro, Match.com and several large online dating websites. She will be talking about getting featured in the press, publicity and how to position your blog to sell your brand and bring in clients.
Saskia Nelson
Founder of the successful ‘Saturday Nights Alright’ dating photography business, she is the only dedicated dating photographer in the UK. Not only will you have a mini photoshoot with Saskia and receive awesome photographs (critical for publicity plan) she’ll be talking to you about the importance of collaboration within the dating industry and giving you her expert insider knowledge.
This really is an amazing opportunity to take those steps towards creating a lifestyle business you love – and one that enables other people to find love! Plus you’ll be the first to receive this training, guidance and mentoring that you won’t find elsewhere in the dating industry, so you’ll be at the advantage of getting a real head start when it comes to the nitty gritty biz stuff too.
To get yourself booked in (please let Caroline know you came via me) and for more info, head to http://www.matchmakeracademy.co.uk. Really hope to see you there!