After talking with thousands of men and women about their frustrations when dating, it would seem that many a potentially great relationship ended before it had a chance to begin. All too often it seems that a first date is viewed as determining whether ‘it is on, or not on’ rather than an opportunity for many possibilities – including the potential it holds for friendship or romance and love.


As a matchmaker I always encourage clients to go on at least two dates realising that there are many things to gain from doing so such as developing a potential friendship, having the opportunity to practice your dating skills, increasing confidence in sustaining a conversation beyond a first encounter and discovering there are more things you appreciate as you get to know each other beyond the pressures of initial encounters. Unfortunately all too often a first date ends up in disappointment and an abrupt ending when it could have offered so much more. 


Instead of looking for ‘what is not there’ on a first date, spend some time appreciating the things you may have in common. Asking your date questions about themselves, their families and their friends may open up shared possibilities and networks that you did not expect. Ask questions that are open ended (who, why, how) rather than those that may only elicit a yes or no response.

Listen more, speak less! We’ve all heard this old adage and it rings true in a first date situation. Understand that your date may want to impress you and is keenly describing all their qualities in order to do so. Don’t be put off by this on your first encounter, understanding that especially men like to show off their feathers!

how to avoid those awkward first date conversations


Be yourself first and foremost. If you are feeling nervous (and chances are you both will be!), say so and let your date know that you are looking forward to getting to know them.

Practice makes perfect and this is true for first dates as well. Think about the other dates you may have had in the past that went well, or not so well, and try and learn from them. Practicing some questions with a friend or trusted confidante can also be a good opportunity to get another point of view. For women especially, showing your softer more vulnerable side can help your date to open up to you. This isn’t a business meeting, so your work persona can be left behind!

Give yourself plenty of time to get ready for your date. If you are driving, map out your journey beforehand so you know what the traffic will be like and where to park. Likewise ensure you know the way to your meeting spot on public transport if that is your mode of travel. Having to rush because you are late or ill-prepared is a sure fire way to amp up your nerves!

Wear something that makes you feel good and is comfortable. There is nothing worse than fidgeting throughout your date because of your outfit! 


Many men exhibit what we like to call ‘The Peacock Phenomenon’ on a first date. They strut their stuff, fanning their splendid feathers to attract the hen, but in the meantime forgetting to ask any questions of, or get to know, their date. 

When you have an initial date with a woman with a demanding career, I strongly recommend avoiding conversations to do with her work…it will prevent her from relaxing. Topics of conversations about common interests such as travel, movies, sport or music can help you to both to be at ease.  Activities such as visiting an art gallery after a morning coffee then sharing lunch or walking in the botanical gardens or along a beach while chatting can help to bring her real self to the fore.  

If you arrange to meet after work, be aware that the demands of her day may have left her stressed and needing to unwind. Talking about topics unrelated to work over a glass of wine or dinner will help her to enjoy the moment and boost her feel good hormones!

Don’t look for what is missing at the outset. A first date can be the start of so many possibilities!

Don’t assume she isn’t interested in seeing you again unless she says so. And if you would like to see her again, tell her and arrange a time to call or meet and stick to it!