If you’ve ever used an dating site or app, you know that someone’s opening message online can make or break the conversation. Why just say “Hey, how’s it going?” when there’s so much more you can say? The new year is a great time to make new dating resolutions for yourself, update your online dating bios and pictures, and just be more focused when it comes to online dating and connecting with matches you truly want to connect with. And who knows? You could end 2018 with a new relationship.
And online dating conversation starters is where it all begins. “Whether you choose to initiate conversation on a dating app or face-to-face with someone you’re interested in, it’s always important to have a great conversation starter in your back pocket,” Kate MacLean, resident dating expert at PlentyOfFish, tells Bustle. “A thoughtful question or reference to your date’s hobbies and interests will likely result in an exchange of information that can tell you a lot about someone and, more importantly, whether you’re compatible or not. The holidays also provide plenty of material for singles to talk about, from what they did on their time off to what their upcoming plans are for New Year’s Eve and beyond. A great conversation starter can lead to more meaningful conversations, better first dates, and new relationships.”
To see what online daters’ messages look like these days, PlentyOfFish surveyed more than 2,500 users 21 to 60 years old. They found that summer is the easiest time to ask someone out, with 32.7 percent of respondents saying so. Winter, on the other hand, is the hardest, with 14.7 percent — perhaps because of cuffing season and people’s desire to stay in more because of the cold weather? As for people who don’t ask potential dates out over the holidays, fear of rejection came in first place, with 58 percent of respondents stating that as the reason, with 21 percent saying there’s too much pressure to do so.
1“What Are Your Favorite Things To Do On Weekends?”
I think this question is *very* telling of someone’s personality. For instance, if all their answers point to staying in and watching TV shows and movies, but you’re more of an outdoorsy and active type, this match may not be for you.
2“What Is Your Favorite Type Of Food, And Why?”
This question is also revealing of your potential date, as they may be a hardcore vegetarian or vegan when you’re more of a carnivore. For instance, I once dated a vegetarian who could not kiss me if I had recently eaten meat… unless I brushed my teeth first. Talking about our favorite foods in advance would have definitely helped.
3“What Are Three Words That You’d Use To Best Describe Yourself?”
I love that this question is limited to three words, because then you really have to think about the best three words that describe you. When I used to write people’s dating profiles for e-Cyrano.com, instead of three words, we’d use three sentences encapsulating those words. So instead of saying you’re “athletic,” you’d say, “I hike for an hour every morning.” However, words or sentences, as long as you choose the best three that describe you, you’ll get the conversation moving.
4“When Was The Last Time You Really Laughed, And What Made You Laugh This Hard?”
Seeing what type of sense of humor someone has helps, too, since you can gauge if it’s similar to yours or way off track from what you find funny. Maybe jokes and comical situations that they find innocent, you find vulgar, or vice versa.
5“Where Is Your Favorite Place In The World, And Why?”
Where someone chooses to spend their free time can tell you a lot about them. Do they staycation or go somewhere across the world where they’ve never been before? And then, what do they do there? One first online date I’d had mentioned his love of traveling in his dating profile, yet, in person when we discussed his favorite places to travel, they were all local — he’d never left his own country. That’s fine, though not what I expected, and also not similar to my more nomadic, country-hopping life.
When it comes to what someone is most proud of in their life, this, too, can tell you a lot about their personality. Is it about their promotion at work? Or is it about helping their 88-year-old grandfather pass his driving test at the DMV?
7“If You Had A Theme Song, What Would It Be?”
More and more apps these days let you add your favorite songs to your profile. For instance, Tinder lets you choose an “Anthem” wherein you choose your favorite song, and Bumble lets you pick a few of your “Top Artists on Spotify” to appear below your dating bio. With Happn, you can even send matches songs through Spotify so you two can learn more about each other’s musical tastes. Of course, not all users state their favorite songs. But whether they do or don’t, talking about their theme song with them is a great way to start talking.
8“What Is The Most Meaningful Thing Someone Could Do For You?”
This question will also let you know your online dating match’s personality to see how they define “meaningful” — from an unexpected compliment someone gave them to a homemade birthday card their niece or nephew made for them.
9“Would You Rather Inherit Money Or Work For It?”
Any money-related talking will reveal a lot about your potential date, too. Since you cannot yet see how they treat money IRL, this question will show you a glimpse of their money mindset. And, as you know, money is a big factor in relationships.
10“What Is The First Thing You Do When You Wake Up In The Morning?”
Everyone has different morning rituals, and what your online match does when he or she wakes up can give you a peek into their personality. Do they make time to meditate each morning, or do they rush out of bed and out the door?
11“What Is More Important — Doing What You Love, Or Doing What You’re Good At?”
I think this is an *excellent* question to see whether someone is really pursuing their lifelong goals and doing something they’re passionate about… or settling for less. No matter which response they choose, it will be fodder for many more conversations and allow you to see how motivated they are in life, career-wise and otherwise.
12“What Is The Most Spontaneous Thing You’ve Ever Done?”
By nature, some people are not as spontaneous as others, and that’s OK, if it’s OK with you. While some people may consider going to a new coffee shop before work to be the most spontaneous thing they’ve done, others may consider an impromptu road trip across the country to be their answer. If your answer would be more the latter and you seek someone with a similar spontaneous spirit, this is a great question to see if your definitions of “spontaneous” match.
So, the next time you match with someone online or on a dating app and are staring at the blank space where a message should go, now you have 12 ideas of what to type there. With 2018 a few days away, now is as good a time as any to test out the above questions.