Em's a 20-something who's reluctantly navigating dating apps while simultaneously pursuing her studies in social science.
What Do I Ask Her?
All of my friends think that dating sucks, and I have to agree with them. After all, they're always bent over their phones swiping right and left, and I'm just over here like, "Hey, maybe you should look up! There's a lot of cute people right freaking here."
If you want to make a meaningful connection with someone you're interested in, you'll need more than an algorithm—you need to be genuinely curious and be invested in getting to know someone outside of their profile. One way I've been able to quickly tell whether or not I have traction with someone is by what kinds of questions they ask me when they're getting to know me. Nothing turns me off faster than the tired, "You wanna hang out at my place tonight?"
If you want to just hook up with someone, stick to your boring app. If you want to land a date with a girl you really like a lot (or to find out if she's your type at all), read on.
If You've Just Met Her
Here are some great questions to get you rolling if you've only just met this person.
- How do you know so-and-so?
- Where's your favorite place to hang out?
- How long have you lived here?
- Where's the best place to get food around here?
How Do You Know ____?
The easiest and quickest way to strike up a conversation with a girl you like but don't know at all is to ask her something seemingly innocuous that has the potential to open up a whole back history if she's willing to share. Say you meet a girl during a party or a group hang, just ask her "How do you know Em? (or whoever you're hanging with.)"
Not only will you get an idea of how she fits in with your friends, you might find out that she knows Em because she's dating Em's brother (bummer!) or that she just moved here, knows Em from her new job and is looking to make some friends here (nice!).
Where's Your Favorite Place to Hang Out?
If you feel like things are going well chit chatting with a girl you just met, you could ask her "Where's your favorite place to hang out?" Her answer can tell you a lot about what you might (or might not) have in common, like that she's at the bar every night while you're reading at the bookstore across the street.
It can also open up an opportunity to invite her to that favorite place to hang out one-on-one if you're still interested.
Plus, if she declines your offer and doesn't take a raincheck, you'll know she's not that into you.
How Long Have You Lived Here?
Another great way to get to know someone is to find out how long they've lived in your town. Whether someone's lived in the same place their whole life or moved around every few years because their mom was in the service, this question can lead you down a long path of conversation, anecdotes about growing up and places you might have in common (who knew you went to kindergarten together?!).
Maybe you'll even branch off into dreamy talk about all of the places you'd love to visit.
What's the Best Place to Get Food Around Here?
Here's another question that can help you gauge her interest in you - ask her where the best place to get food (or even a particular kind of food like sushi, pizza or vegan burrito bowls) is and then invite her there for dinner with you.
If You Work Together
These questions are great in a work environment.
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- I'm all caught up, is there anything I can help you with?
- I'm about to go on lunch, want to come with?
- Is there a better way to do this?
- What are you listening to?
I'm All Caught Up, Is There Anything I Can Help You With?
It can be precarious navigating a workplace crush but it's also kind of inevitable for most single people. If you find yourself crushing on your desk mate don't get weird and start asking super personal questions. For one thing, it's unprofessional and for another, it can come off as creepy.
Still, there are ways to show and gauge interest without totally revealing how head over heels you are. One way to do this is to make yourself a little more available and a little more friendly to this girl than you are with other coworkers.
If you're all caught up or you have work you can set aside for later, ask her if there's anything you can help her with. Just don't frame it in a way that's condescending or that says, "You seem incapable, here let me show you how to really load this printer - you're welcome."
Instead try to smooth the edges of your question like "Eh, today's been crazy but somehow I've got all of these emails sent before lunch. How are you doing, could you use a hand?" Girls like a dude (or a gal) who's willing to help in a humble, genuine way.
I'm About to Go on Lunch, Want to Come With?
Girls love food because they're humans and as with all other humans, they need calories to continue their day.
Now, this tactic isn't as cute if you're only allowed to eat lunch within the building you work in because then it just looks like you're needy and want someone to entertain you while you eat. It can come off as inconvenient, especially if she was planning to text with her mom on lunch or catch up on Netflix in her car while she snacks on an entire box of Ritz.
But if you're able to grab something down the street this is a fun way to take her on a mini-adventure and give her a break from the everyday while also getting some time alone to get to know each other.
Is There a Better Way to Do This?
If you straight up ask her for help with something she knows you're capable of she's going to know you're just trying to get her to "accidentally" brush your hand.
Instead, ask her if she knows of a better way to complete a task or process in a more streamlined way. If she's up for showing you her way of doing things you'll get a chance to vibe off each other for a few minutes.
What Are You Listening To?
If you work in an environment that allows you to pop in your air pods, there's no better way to really get to know someone than to find out what they're listening to. It's a completely neutral question with answers that say a lot about whether or not you share anything in common.
If You Go to School Together
Are you and your crush in school together? Give these questions a try!
- Do you have any pets?
- Got any advice on professors for next semester?
- Do you know anyone who's hiring?
- I'm grabbing something from the vending machine, what can I bring back for you?
- What's your favorite thing to read lately?
Do You Have Any Pets?
If she loves to talk about her pets this is a super way to spark a friendship with her. I could honestly go on about my cats for a full 15-minutes without stopping to catch my breath.
This is a huge problem for some guys which makes this question an effective tool for weeding out cat-crazy girls who start pointing out each cat's individual hairs on her sweatshirt, explaining the night-time play habits of each one.
Got Any Advice on Professors for Next Semester?
Here's a good way to get to know what she's majoring in, what subjects she enjoys and which ones she hates. Likewise, if you're further into the semester it'll give her a chance to vent and you might unintentionally hear all about her anxiety disorder, her exam fears and even her crush on a professor. Getting to know the most difficult parts of someone first can be strangely bonding.
Do You Know Anyone Who's Hiring?
Asking her who's hiring will give you some insight into if she has a job and where, and what types of connections she has.
While it's not the most interesting thing about someone, it's added insight and a conversation starter that doesn't scream "I've been staring at the back of your perfect neck through this entire lecture."
I'm Grabbing a Drink/Snack From the Vending Machine, What Can I Bring Back for You?
As mentioned before, girls love snacks because who doesn't? Asking if you can bring her back one is a kind gesture and bonus, you can bond over your shared love of bite-sized Oreos.
What's Your Favorite Thing to Read Lately?
Finding out what, if anything a girl is reading at the moment gives you a glimpse into who she is outside of academics and what really ignites her interests. Plus, it gives you a chance to share yours too.
If You Already Know Each Other Pretty Well
Do you already know your crush fairly well and need help getting to know them on a deeper level? Give one of these a go.
- What's good for podcasts?
- Do you ever think about starting fresh somewhere new?
- Why do you think that things didn't work out with your ex?
- Did you ever make your pets talk growing up?
- What's something you feel like most people get wrong about you?
What's Good for Podcasts?
Podcasts are oddly personal and I don't tell just anyone that the one I listen to habitually is titled "My Favorite Murder" because if they don't know me well they might not want to get to know me at all after that.
So, if you know someone fairly well, now's as good a time as any to share your favorite podcast and get to know each other even better.
Not only does it help you discover new content for your own listening pleasure, it'll give you things to talk about as you catch up on her favorite podcasters and their seriously quirky inflections.
Do You Ever Think About Starting Fresh Somewhere New?
This one might not be for everyone, but it's a clever way to fantasize with someone. I once plotted an entire new life in France with an ex. Of course, I'm still trudging through spring snow in the northeast, but daydreaming together can be a very nice way to get to know someone on an intimate level.
Why Do You Think That Things Didn't Work Out With Your Ex?
But don't say "ex" because that's impersonal. If you've known this girl a while and wounds aren't so fresh and the conversation seems appropriate, ask her why she thinks things didn't work out. If she's ready to have that convo you'll get to know things she probably hasn't shared with you before about her feelings, what gets to her, and what makes her feel valued - all important things to know about someone you care for.
Did You Ever Make Your Pets Talk Growing Up?
If you don't already know this about her, this is a super important thing to know because those of us who did are just waiting for someone to tell us it's okay so we can start making our pets talk in front of you.
What's Something You Feel Like Most People Get Wrong About You?
We all feel misunderstood, and there's nothing more cathartic than being given the chance to explain yourself without judgment to someone who wants to know the parts of you they often feel they can't share with others. Giving her a chance to be vulnerable (and not taking advantage of it) shows her that your interest in her goes beyond the surface.
How to Keep the Conversation Going Once You've Started Getting to Know Her
Make It an Ongoing Conversation
Obviously you can't just ask her question after question. This isn't an interrogation! If the hope is to get a conversation going and learn more about each other, follow dating coach The Wing Girl Method for "threading" to keep the conversation fresh and interesting for both of you.
This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.
Questions & Answers
Question: I really like this girl at school and lately, we've been texting each night but some nights she doesn't respond, how can I know if I'm texting her too much?
Answer: Don't text her every night. Since she doesn't respond to your texts some nights, there's a good chance you're texting her too much already. Like you, she has other stuff going on, like homework, family stuff, and her other friends. I would give her a chance to be the text-initiator and limit yourself to texting her two or three evenings a week. If she misses you, she'll definitely fill in those gaps by texting you on her own when she doesn't hear from you.
Question: What is the best way to win a girl over through texts?
Answer: For me, I appreciate a guy who checks in on me once every couple of days. A text like "Hey, how's your week going?" can open up a conversation and let her know that you're thinking about her without feeling pressuring either. Two things that will definitely not win me over are texting me when I'm sleeping (like any time after 10 PM) or texting me too often when we don't know each other well in person.
I think a great way to win a girl over through text is to just converse with her the same way you would in person - with regard to her space and letting her have an equal part in the conversation as she gets to know you!
Question: Do girls like shy guys who don't have a lot to say at first?
Answer: Yes! I mean, I think it's fair to say that not everyone is everyone else's cup of tea. A shy guy might be a turnoff to some girls but is a total turn-on to others. If a girl doesn't seem into you when you're shy, then she's not for you. You don't want to pursue a relationship with someone you can't be quiet (or yourself) around. Be you and you'll attract the type of person who will love you for you.
Personally, I've always been attracted to shy and quiet guys, and I know I'm not the only one!
Question: This girl at work likes me but she has a boyfriend, what should I say to her to get her to pick me?
Answer: There's nothing you can say. Here's the thing: she already has a boyfriend. She's already chosen her boyfriend. There's nothing you can really do to sway her to break up with her boyfriend even if she does say that she likes you. There's a lot of things that keep a girl with her boyfriend even if she's not that into him anymore. Maybe she's afraid of what life would be like without him or maybe there would be financial implications like having to find a roommate or dealing with debt they accrued together.
Your best bet here is to take a few steps back and do your best to pursue other people until or unless she becomes single.
© 2019 Em Clark