Our Best First Date Stories & Tips

Ahh, the first date. One of the must gut-wrenching, sweat-inducing human experiences ever. You’re probably perspiring just thinking about it. We get it. That’s why we rounded up the best first date stories and tips (including one from yours truly) from seasoned relationship experts and writers to help you with your quest to conquer the first date and make it the best one ever. From romantic dates abroad to a concert in NYC, here’s what you need to know to turn a first date into a second one.

First Date #1: Keep Questions Creative

From Shannon Tebb, dating consultant, Shanny in the City

“It didn’t feel like an interview. He asked me creative questions about what I am passionate about in my life rather then what do you do for work. He genuinely listened to what I had to say and didn’t interrupt me and make the conversation all about him.

He had a plan. He picked a great restaurant and put effort into organizing the date, which showed confidence. He put effort into his appearance. He smelled great and was well groomed. There was instant chemistry.

He made me laugh. A great sense of humour is very important. Being able to laugh with someone creates comfort and builds a connection. He complimented my personality or energy rather then focusing on one of my physical attributes.

He wasn’t afraid to show me affection in public. He held my hand as we walked down the street. This showed that he was proud to be with me and wasn’t afraid to show this to the world.

If we travelled home independently, he checked in with me to ensure that I was home safe. He sent me a follow up text message saying how he had a great time with me and looked forward to seeing each other again.

I didn’t want the date to end and was left with butterflies and excitement.”

First Date #2: Don’t Be Intimidated

From Kat the Sexpert, CEO of Ohhh Canada

“My best date ever happened overseas. It was a fancy restaurant, we met in a hotel lobby. I was all dolled up, and he looked amazing, too. Both of us had clearly made an effort to impress.

He seemed to have everything all planned out: he hard-to-get table by the window overlooking the city, the best wine to order, the impossibly chic cocktail lounge with the live band we went to afterwards . . . and the condoms that were hidden somewhere on his person that just “appeared” on the bedside table of my hotel room.

I am a strong personality, and so sometimes I intimidate men. He never seemed intimidated, but nor did he try to “be the man” in the classical sense. Instead he was thoughtful, powerful and engaging. The best way I can describe my best date ever? Smooth and intense.”

First Date #3: Meet over Live Music

From Suzannah Weiss, writer for BustleGlamour, and more (view her work here)

“One of my favourite bands, the Finches, was playing nearby, and I invited a guy from OKCupid to come with me. The concert venue was also an art gallery with drawings of peculiarly emotive penises on the walls, as well as a vegan restaurant. Over tofu curry, we finished each other’s sentences. The lead singer of the Finches made eye contact with me as I mouthed the lyrics to “The House Under the Hill”. I met her after the show, and we talked about astrology.

My date and I played a twenty-questions-like game called Boticelli on the drive home and made out in his car before he dropped me off. He even invited me to hang out again in a few days—yet soon after, he did a total 180 and fired off a litany of reasons he didn’t want to see me again, including “astrology is dumb”. That’s how I learned that first impressions can be fleeting—and that sometimes, the musical connection you form on a date can be more lasting than the romantic one.”

First Date #4: Make it Easy For Her

From Deanna Cobden, Dating Coach

“The date activity itself was a pretty standard drinks and appetizers, but it was the little details that made it special. We’d met at a bar the week before, so first he called me on the phone and we set a date. Instead of the back and forth (“What do you want to do?” “I don’t know, what do you want to do?” the worst!), he made a plan and suggested a couple of places that were on my side of town to meet. I really appreciated that he had taken my location into consideration. He kept in touch during the week with a few quick texts and confirmed the morning of. Again it really showed he was thoughtful, there was no disappearing leaving me wondering if we were still on.

The conversation was easy, playful and fun, I love a smart guy and we really clicked. At one point it felt like it was just the two of us in our own world. When the check came, he grabbed it right away, again this just makes it easy, no awkward moments wondering if I should offer or make the purse grab. We decided to check out a place down the street that had a live band and walked there hand in hand. The night ended with a kiss, plans to see each other again and he got me a cab home.

Actually on side note he had actually offered to pay for my cab there, definitely a first for me. I didn’t take him up on the offer but I really appreciated it. By now I’m sure your sensing a theme—thoughtfulness! Women love a guy that makes them feel cherished and special and his thoughtful nature made a first date, which can be a nerve racking thing effortless and easy and set the tone for an amazing time.”

First Date #5: Simplicity can be Bliss

Brianne Hogan, freelance writer extraordinaire

“I don’t go out on many official “first dates” because most of the men with whom I’ve been involved are usually friends or acquaintances, so “hang outs” often blur into “dates.” So when I actually go out on a legit first date, I am always super excited and pleased that a man had the courtesy—and the balls—to officially ask me out. I think a lot of women can relate to this whole “is this, or isn’t this a date?” So I think being clear about your intentions will not only save a lot of time and confusion, but it’s also a huge turn on.

Okay, so back to the date. It was at a hole-in-the-wall sushi restaurant and it was lunchtime, which goes to show fancy doesn’t always mean memorable. Sometimes simplicity is bliss. He picked the place—which I appreciated—and when I entered the restaurant, he was already there. Tardiness is a turn-off. If you’ve arranged the date, you should definitely be the first one there. Actually, even if you didn’t arrange the date, you should be early. It demonstrates excitement and respect, and seeing your date already at the table guarantees that whole “butterflies in the stomach” feeling, which is an awesome way to start a date.

He held my hand during the meal (not the whole time—we did have to eat) but it was enough to show his affection for me without being overbearing and aggressive. He paid the bill. Call me old fashioned, but I think going Dutch on a first date is more like a business transaction than a romantic interaction. Afterwards, we took a walk and chatted, which was sweet. It gave the date, and us, more time to connect rather than doing the whole ‘eat and run’ thing. At the end of the date, he left it up to me whether we would kiss or not. I was majorly into him, but I wanted to take it slow so I kissed him gently on the neck. We later dated for a while.”

3 More Tips

From Dr. Jess, Desire Resorts’ Official Sex & Relationship Expert

1. Don’t try too hard. If you try to force a connection, you might find that it wears off once you get comfortable with one another. I’m not suggesting that you shouldn’t give the connection time to grow and put some effort into it, but if you have to go bungee jumping on your first date to make it thrilling, don’t be surprised if the thrill doesn’t last.

2. Don’t analyse. Just be. Enjoy the moment as opposed to analysing his/her every move, word and gesture. You want to be a participant—not a spectator.

3. Do something active. You’ll never run out of things to talk about if you’re active. My first date with my husband involved a trip to High Park in Toronto to walk, hike and roam the gardens. It has been almost fifteen years and we still hike, play sports and stay active together. And we almost always follow a day of activity with wine!

Brianne Hogan is a freelance writer based in Toronto, something of a humorist, and considers herself more Bridget Jones than Samantha Jones. Though she won’t reveal which parts, she will admit to liking emotionally unavailable men and drinking lots of wine.  You can follow her on Twitter  @briannehogan.

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