How To Ask Someone On A First Date

Many of you were struck by the title of this blog post because you’ve never actually asked someone out on a “real” date before.  Perhaps you have always stuck to dating people in your friend group where your past boyfriends have transitioned seamlessly from being just your friend to your boyfriend. You never really had to ask them, it just happened. Now you find yourself single and wanting to date again!

If you are a first time dater, here are the most common scenarios followed by the most effective ways to claim a date with your crush!

Scenario 1: You meet online

You’ve decided to pop into your PlentyOfFish profile and bam, his profile jumps right off the screen. His main picture places him easily in “Major Babe” status; but you know the game all too well and cautiously click through the rest of his photos. This is too good to be true; he is giving you the perfect taste of who he is and what he likes to do for fun (he heli skis in his spare time?! Major Babe status has just been taken to a whole new level!).

So you’ve creeped every photo at least 8 times over and studied his interests and bio until you have them memorized word for word. But what’s next? How do you move from class five creeper to his date? Well here’s an idea…you could just ask him out!

Ladies, it’s 2016, you don’t have to wait for the guy to make the first move! Sign into your profile, go to send him a message and write, “Hey (Name), I’m going to be honest here, I have looked at your profile at least twice in the past hour and it took me another half hour to think about what to write to you. I think it’s really cool that you (name one of his interests)! Hit send; now the ball’s in his court!

If you don’t receive a response, don’t worry about it; move on and try again with a new prospect! Rejection can be a kicker, but it’s far more worth it to put yourself out there knowing you tried than sitting back and wondering what could have been. If you do get a response, jump up and down and exchange a few more messages until you confidently ask “Let’s meet up this Saturday, are you free at 8pm for a drink?”

Boom, you got a date.

Scenario 2 : You meet in person (gym, bar, coffee shop)

I am going to focus on the gym meet for this one as it can be one of the hardest locations to ask someone out.

You’re profusely sweating on the treadmill when in walks “Major Babe” of the gym! You look up, make eye contact, then increase your lame jog to full on iron man sprint just to impress him. It’s been about three weeks since he first walked in and you so badly want to coincidentally run into him at the water fountain without looking like a complete stalker who pre-planned every step. The best moment to approach a gym babe is right after their workout, NOT when they are lifting or on a machine. Catch them on their way out of the door with a simple, “Hey, you crushed it in there! You made me want to work out harder.” Followed by a smile. I wouldn’t ask him out after this first interaction as the gym babe takes a couple days to warm up; but once you find yourself having a conversation the next couple of sessions, go for it!

Scenario 3: You meet at work

This one can be tricky and I haven’t been one to date within the workplace, but let’s get real; it happens often. You spend 8 hours a day, 5 days a week with your coworkers. It is important to exercise caution when asking out an associate. Before you jump right into it; remember, you will see this person every single day for however long you want to stay in your job. Take time to think this one through before you dive head first. If the connection is undeniable and you see a potential future with this colleague, the safest approach is to ask them for a casual apres work coffee/drink first to see what your dynamic is like outside the office. If the feelings are mutual and you both know it, ask them out again.

Scenario 4: You meet through friends

Your bestie is thrilled because she’s found out her boyfriend’s friend is single and he is just your type. She has described him in full, from what he does for work, to what his favorite breakfast food is (this must mean he loves brunching just as much as you). He sounds pretty damn incredible and your friend is already planning a future double date, so you better get on it and ask him out! You ask your friend for his Facebook name because you can’t fathom asking him out without a solid creep sesh first. My best advice is to try and avoid this step and go straight to setting up a date, because your friend has already laid it out for you. Ask your friend for his number and send a quick message saying “Hey (Name), I got your number from (name of friend) and thought it could be fun to link up this weekend. Do you want to go for a drink/coffee on Saturday?. With this scenario you may have a slight upper hand because you both have friends in common.

Maybe you have found yourself in all these scenarios before but never had a clue how to approach any of them. I hope this post encourages you to go for what you want and not be afraid to put yourself out there. Even if you start with a simple smile, hello or text message, you are one step closer to finding your next date!

Kate Maclean

Posted by Kate Maclean

Kate is the PR Generalist at PlentyOfFish. Like a kid in a candy shop, Kate’s favorite things to do are eat mass amounts of sushi, spoon her cat Snoop Dogg, and hike the great Canadian wilderness. Her favorite quote of all time is “People who love to eat are the best people” -Julia Child.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.