20+ Questions To Ask A Date Online - Wingman Edition

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Stuck at "Hey"? Here's the questions you can ask for yourself or on behalf of your BFF.

We all know getting stuck at the dreaded “Hey” stage after a match can be frustrating. This is when you need to ask the right questions to keep the conversation going.

At Wingman, we let your friends do the talking. 

We all have a single friend that we’re ready to play matchmaker for but how do you know if the person you’re setting them up with is the right person for them?

As a wingman, you need to be asking the right questions in order to get them the best possible match. It’s your chance to squash the red flags for your single friend and make sure their potential partner is in it for the right reasons.

It can be hard to walk the fine line of coming across as a protective friend vs interrogator so make sure you have your friend’s best interests at heart.

Whether you’re an online wingman or IRL wingman, here’s the questions you need to ask to land your friend their perfect match.

Factual - Ask these questions to give your friend the base-line facts about their potential date

How long have you lived in [insert state or city]?

What do you do for a living?

Have you had your vaccine yet?

Are there any lockdown activities that you took up?

Are you the youngest or oldest in your family?

How long have you been single for?

Emotional - These can be tricky to ask a stranger but worth it to find their real intentions.

Do you prefer someone’s who an introvert or someone who’s an extrovert?

Do you think opposites attract?

How do you feel about being Single?

What’s one thing you learnt about yourself from the pandemic?

Do you have expectations on what your partner should be like?

Values - Don’t just rely on just the outside aesthetics to tell you about them, ask what really matters to them.

What’s your one deal breaker?

How important are having hobbies in common to you?

What do you think of ghosting?

What’s one thing you hate about dating?

Do you think arguments are a good thing or a bad thing?

How important do you think communication is?

Fun - Not a fan of asking heavy-hitting questions? You can still ask these lighthearted ones and get an idea of their sense of humour.

How would your mum describe you?

What one song would get you on the dance floor?

Which celebrity are you most like (in terms of personality)?

What is your ultimate fancy dress theme?

Your go-to dance move?

What did you dress up as for Halloween?

What’s one show you’ve watched recently that’s so good?

If you had to sum up your life so far as a movie plot, what would it be?

The best wingman is one who listens, is active and communicates on behalf of their single friend, not in spite of it. Remember, this is a fact-finding mission, you’re here to help not interrogate. While it can be hard to reserve judgement, ultimately you want to give your friend the facts and let them decide. 

Looking for a way to be an online wingman for your single friends and ask the right questions?

Download Wingman app and matchmake your friends.

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