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Two Mistakes To Avoid When You Start Dating

How do you greet someone on a first date?

Do you keep things polite with a handshake? Presume a certain level of affection and go for a hug? Add a kiss on the cheek? Maybe avoid the issue altogether and just stick with an awkward smile?

I genuinely don’t know the answer! There have been times when I’ve gone for the handshake and my date has gone for the hug. Another time I went for the hug and my date’s response was comparable to that of a fainting goat. Once, we were both so confused that we just decided to fist-bump.

Dating as a young adult can be complicated. What I’ve learned while navigating the handshake-or-hug tension is that there’s no one-size-fits-all formula. Yet while there isn’t a single right way to date, there are definitely wrong ways to date.

Two approaches in particular are constant culprits for starting a dating relationship on the wrong foot:


In an attempt to woo your prospective partner, you go all out. You organise a full day of activities or take them to a restaurant so fancy you pay $12 just for the table water.

Whatever you do, you go ‘all in.’ You aren’t leaving even a shred of doubt in your date’s mind about your romantic intentions.

The problem with the ‘all in’ approach is that it can create a lot of unnecessary pressure – for both parties.

The person who plans that date can end feeling like they need to constantly impress the other party. The unsuspecting recipient of an ‘all in’ date can be left feeling uncomfortable about the amount of time (and often money) that has been spent on him/her.

Furthermore, when an ‘all in” date doesn’t go well, it can turn into a kind of date-imprisonment for either/both of the parties. It’s hard to politely excuse yourself from a situation when you are only one hour into a four-hour romantic river cruise.



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At the opposite end of the dating spectrum from the ‘all in’ is the ‘chill.’ This approach to dating typically involves inviting someone to a nearby couch, park or group setting to, well, “chill.”

While your goal in taking the chill approach might be to create a casual, low pressure setting for the date, the problem with the ‘chill’ is that it often leaves the other person with no freaking idea what is going on.

You might be perfectly comfortable in your  sweatpants, but he/she is probably wondering what you plan on doing for the next hour, whether you’re going to share your bag of Doritos and most importantly, whether the two of you are even on a date.

The ‘chill’ approach to dating can also cause undue hurt or confusion where the other person doesn’t understand your intentions. He/she might assume that your invitation to“grab coffee together” is a purely platonic opportunity to sample the varieties of almond milk available at your local café, while you intended it to be the start of a dating relationship.

Finally, the ‘chill’ approach can be perceived as a lack of effort on your part. The person you’re asking out probably doesn’t expect a 4-stop tour of the vineyards in your region, but I’m sure they want to feel like you care about getting to know them.


As you’ve probably figured out, the solution is a balance between the two extremes.

If you want to start dating someone, be intentional. Put a bit of effort into planning your dates and make it clear to the other person that you are, in fact, asking him/her on a date. One method that I’ve found works well is to use some variation of the phrase “I’d like to take you on a date.”

However, try to keep things relaxed. Your goal for the first few dates should be to create a low-pressure setting where the two of you can start getting to know each other. You can always postpone the hot-air balloon ride until you’re a bit more serious!

Wondering how to put this into practice? Stay tuned for my next post. Ever been on a terrible first date? I want to hear every detail in the comments section below!

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3 People Replies to “Two Mistakes To Avoid When You Start Dating”

  1. Nick Cardone

    Great article. I love the 12 dollar table water reference!

    1. Thanks Nick! It’s an example I’ve actually experienced in real life!

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