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How to Have a Successful First Date With a New Guy

July 12, 2021
How to Have a Successful First Date With a New Guy

First dates can feel like so much pressure! 

  • What do you wear when you want to look glam, pretty, sexy and intelligent all at the same time? 
  • Will a full face of flawless makeup make you look like the girlfriend of his dreams - or come across as shallow?
  • Turn up on time, five minutes early, ten minutes late - or skip the whole thing!!

Ok, let's breathe for a second. Yep, it's a lot to take in. 

And, if you're looking for a long-term relationship and have met a man on the top Toronto Canada dating sites, it can seem that this couple of hours is pretty high stakes.

Let's take a step back, and run through some of the top dating tips from the relationship experts at Best10; after all, every unique relationship starts with a first date!

The Master Class on First Date Outfits for Women

We'll start with the outfit. It's super tricky to get the balance right, as most women want to appear cool and casual and yet not look like they haven't made any effort at all.

Of course, a lot depends on what you're doing for this date.

Breaking in a new pair of five-inch heels for a Sunday afternoon coffee and stroll around the park is not going to do you any favours - and probably result in some nasty blisters to boot!

Likewise, if you're heading for a romantic dinner date, you're not going to rock up in your boyfriend jeans and your slouching sweater.

Here's what to do:

  • DON'T wear anything brand new. If it doesn't fit right, isn't comfortable, is too tight, or feels weird, you're not going to relax and pay attention to the conversation.
  • DO wear appropriate shoes. Enough said.
  • DON'T try to dress like someone you're not. For example, if you are a converse and shorts kind of girl, that's A-OK; you don't need to pretend to be a prom queen if it's not your style.
  • DO ask your friends for a second opinion if you're having a confidence crisis. There's nothing like having your personal cheer squad remind you how hot you look to boost your self-esteem!

Remember, any man worth his salt will want to get to know the real you, and it's pretty likely he'll have no idea what you're wearing in your profile pic he fell for when online dating in Saskatoon.

Splitting the Bill - To Pay or Not on the First Date?

So, the next tricky bit is cash. Expecting a guy to cover 100% of the bill on a first date is, let's face it, a bit archaic and also slightly unreasonable!

If he offers, or insists, then great - still, you don't NEED to accept if it makes you feel uncomfortable, or you get even the slightest whiff that he's the sort of man who's expecting something in return (run, run, as fast as you can).

Nobody wants to be seen as a gold digger or the kind of woman who feels she deserves to be wined and dined without contributing a cent, so we'd always recommend splitting the check, 50/50. Simple solution.

As a last-ditch, if he really wants to pay and is doing so as a conventional kind of chap who feels he wants to cover the costs, at least make sure you leave a tip and pay for the cab!

Is Kissing a Guy on a First Date Ever a Good Idea?

There are SO many old-fashioned, conservative, and in some ways, judgemental ideas out there about first dates - and the reality is, it's entirely up to you.

Say you've been chatting for weeks through your favourite Toronto Canada dating sites, have spent hours on video calls, and now you've finally met in person you're desperate to progress to your first kiss. I say go for it!

However, there are a few general guidelines to be aware of:

  • Nobody has the right to kiss or touch anybody else without consent, so always tell him you'd like to kiss him.
  • Sometimes, a 'surprise' is fine, but it's vital to assess the situation and ensure you're not making presumptions about whether your date is comfortable taking it to the next base.
  • Test the waters with a bit of arm touching first, and read his body language before taking the plunge.

Just as you wouldn't want to play tonsil hockey with a guy you're not yet sure about dating long-term, it's vital to respect boundaries here.

Also Read: Which are the Most Popular Platforms for Online Dating in 2021?

How to Cope With First Date Nerves

The nerves can be one of the worst parts of a first date. Clammy hands, racing heartbeat and stuttering sentences are all typical signs that you're feeling anxious.

A great way to break that tension is to find humour in it!

Having someone you've met online dating in Saskatoon feel nervous about meeting you is always an ego boost, and it's likely to ease some of the friction your date is undoubtedly feeling too.


  • I've changed three times for this date; I had a real panic about what to wear!
  • Sorry, can I have a glass of water? I'm super nervous about finally meeting you!
  • It's so great to meet you in person - I've been thinking about this all week!
  • Apologies for my stuttering; I think the nerves have got to me a bit!

You can see that these are all light-hearted ways, to be honest about the fact you're feeling anxious. It's also helpful to be upfront if you are struggling a bit and shows that you aren't afraid to talk about your feelings (and don't usually forget your own name...).

The thing is that a first date is just that - a first date.

It can be nerve-wracking if you're serious about this guy and want to make it work. However, wearing the wrong dress or mumbling when ordering your coffee isn't going to make any difference to an authentic connection that's destined to go somewhere.

Take it easy, have fun, and don't let the anxiety make it feel like any wrong move will spell disaster!

Lauren Edwards-Fowle
Lauren Edwards-Fowle
Lauren is a freelance writer passionate about how we develop rewarding experiences, and overcoming the barriers we face to living our best lives. Lauren writes regularly about the modern world of dating, relationships, parenthood, and social dynamics.