5 Awkward Questions You Should Always Be Prepared To Answer On A First Date

by Jaemie Sures
Jayme Burrows

First dates can be exciting, awkward or uncomfortable. Some are better than others, and some are worse than others. The first date is basically used as a screening to determine whether or not the other person is relationship material, and to see if there is a possible connection. When dealing with matters of the heart, there is always the possibility of touching on some unnerving topics.

Treat your first date like a job interview, and do a little bit of prep before entering the dating battlefield. Here are five questions you should always be prepared to answer:

1. Why are you single?

This question is guaranteed to come up, so do not respond with a detailed story of all the trial and tribulations of your dating past. Do not under any circumstances take this as an opportunity to trash talk your ex. This just sends red flags up in your direction. Try to be vague and concise.

When your date asks you this question, choose a response that is relevant to your situation. You can either be recently out of a relationship and taking time for yourself, making your career a priority, exploring the world or currently screening candidates to be the father figure for your cat. (OK maybe don't use that last one.) Hopefully one of these answers can lead into a more desirable topic of conversation.

2. How long have you been single for?

If your date did not like your response to the first question, this is a common follow-up question. Sometimes there is a catch when people are too good to be true. Take it as a compliment.

If you have been single for five plus years, just say you have been casually dating and seeing what happens. Mentioning the extended length of time may be a little overwhelming.

If you are recently out of a relationship, mention you were in a long-term relationship, but things didn't work out. So now, you are back on the dating scene. Do not give a precise measure of time. Even though your date asked the questions, this is a conversation better covered on later dates, once you get to know each other better.

3. What do you like to do for fun?

For some reason, this question always catches me off guard. I usually want to say, “Nothing” and shrug my shoulders. Obviously, this is not a desirable response, and it's the easiest way to seem completely uninteresting.

Think about this question before you go on dates, so you can be happy with your response and answer the question truthfully. Everyone has interests; sometimes it's just hard to sum them up.

This answer should be an accurate representation of you life, and they should be topics that you would like to elaborate on. You may enjoy going to concerts, watching or doing sports, being outside, checking out new restaurants or traveling. This question should promote further conversation and perhaps uncover some mutual interests.

4. What do you do for work?

My girlfriends and I are split on how we feel about this conversation starter. I think it really depends on where you are at in your career. Work makes up a huge chunk of your life, so it seems perfectly natural to discuss what you do, unless you have a job you are not proud of. In this case, say what you do and mention what your long-term goals are.

If you love your job, refrain from trying to show off or getting overly technical. Mention a few highlights of your day and a brief description, and then try to move on to a topic both parties can relate to.

5. What do you look for in a partner?

Hopefully your date it not drilling you with all of these probing questions, but if this question comes along, be ready to give an accurate answer. Have the top five qualities you look for ready, and make sure none of them are physical attributes.

For example, I look for someone with a sense of humor and good family values. Decide on a simple statement that tells the other person a little about yourself and the character traits you are interested in. This is a good way to see if your personalities could align.

Dating is supposed to be fun, so try to make the evening enjoyable. Although it is important to get to know each other, you also want to let things happen organically and have the opportunity to enjoy each other's company.

Every date does not have to end in a second date. At the very least, you will have a story to tell, an opportunity to make a new friend or a better idea of the type of person you would never ever want to be with.