Do you feel very nervous before dates? Do you suffer from shyness in social situations generally? Here are some tips to help you relax and enjoy your dates:
- Practise talking to strangers about simple things like asking for directions, comparing products when you’re both staring at the shelf in the supermarket, or asking for a recommendation for a local café or restaurant.
- Practise smiling when you talk. This will put the other person at ease and then they will help the conversation along more.
- Prepare follow-up questions. For example, if someone comments at the bus stop that the bus is very late, don’t just agree – ask them how often they get that bus, if they live locally, what they think of the area.
- Have a specific focus that is not about you. This could be aiming to find out as much as you can about the other person’s job, or interests, or goals. Or it could be to make the other person feel comfortable and happy.
- Arrange active dates that are not just sitting opposite each other in a café, bar or restaurant. Go for a walk or to a gallery so you can talk about what you see and focus on learning new things.
- Prepare some questions in advance. You can use my 140 dating questions (purchase them here for only £5), either just printed as a list, or put them in an envelope on separate pieces of paper and pick them at random to make it more fun. Remember the focus should be on finding out if the person is right for you, not on you making a good impression.
Here are some good simple ones, with follow-up questions:
- When was the last time you had a day out? What did you do? Where else would you like to go? What would be your ideal Saturday?
- Do you like to socialise with a group of friends or do you prefer one to one? When did you last go to a party? Did you enjoy it? Have you ever thrown a party?
- What’s the best thing about your job? If you could change careers and re-train, what would you do? What did you want to do for a job as a child?
- Do you have any hobbies? Do you enjoy sports? Do you like reading? If you could go to a new class or join a club, what would it be?

Do something fun on a date to take the pressure off talking.
- Practise your answers to standard questions such as “What do you do for a job?” Often shy people will give closed answers, such as just stating their job title. Then the questioner doesn’t know what to do with your answer. They may think you don’t want to talk about your job. As well as the job title, you could say where you work, how long you’ve been working there, what you like about it, what your main tasks are. And if you’re unemployed, talk about what you’d like to do or what you enjoyed doing in the past.
- Always ask the same question back. The fact that they’ve asked you means it’s the kind of thing they’re interested in. So follow-up questions would probably go down well too, such as “What do you like about your job?” or “What are the hours like?” or “Is there anything you’d like to change about your job?”
- Both people should take responsibility for “oiling the wheels” to make a good conversation flow more. Try listen to other people talking and notice what is going on. When one is talking, the other will interject with “Mmmmm”, “Right”, “Yes”, “OK”, “Really?”, or “How interesting”, nodding, making eye contact, or laughing. If you find this difficult, listen to the radio and do it along with the speaker, while looking in the mirror to make sure you’re smiling!
- You need to make the other person feel like they’re the most important person in the world while you’re having a conversation with them. Don’t waste precious mental resources on anxious thoughts during the conversation. It is very easy to have two conversations going on at once: one with the other person, and one in your head with yourself, which goes something like this: “This isn’t going very well. My date must think I’m an idiot!” or “I shouldn’t have said that. I’ve ruined the conversation now!” This uses up your limited resources for holding a conversation and then no wonder you find it hard! Stay completely focused on your date and keep making eye contact.
Do get in touch if you’d like some help with developing your conversation skills and getting over shyness or anxiety. I use a graded approach, starting with, for example, asking a stranger for directions and working up to having a longer conversation and asking someone for a date. You’ll feel great even after one hour’s consultation, I promise!

Contact Rachel here:
Nice article with some good tips. Glad you mentioned the listening part Rachel, as being asked questions by someone is pleasurable and engaging when they are genuinely listening. I’ve been half way through answering someone’s question before and they’ve interrupted to ask me another. And then, even faster, they’ve interrupted to ask a third and fourth. Which left me feeling a bit pressured and frustrated. Eye contact when listening and waiting for the person who’s answering to finish helps. As long as they don’t go on too long!
What would your advice be, if you’ve asked a question and the person’s answer just never seems like it’s going to come to as natural end?
I would probably have to interrupt them! I might make a joke and say “Will I be allowed to talk soon?!” Sometimes people don’t realise they’re doing it. Either they respond to your implied criticism or they don’t get another date!