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Dating coach Laura Bilotta shares the cutest, flirtiest, and best texts to send to anyone you LIKE like
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Oof, there’s nothing that’s so simultaneously exciting AND terrifying as hitting “send” on a text to your crush. So, if your head is full of thoughts about your crush but absolutely zero thoughts about what to text them, we’re here to help! In this article, we’ll share real texting and dating advice from thousands of wikiHow readers, as well as expert insights from a team of dating, relationship, and communication coaches. You’ll also find excellent icebreakers for texting your crush, as well as tips on asking out your crush and how often you should actually be texting them.

The Best Messages to Text Your Crush

Dating coach Laura Bilotta says to start with a genuine compliment, like “I’ve been thinking about your smile all day” or “You always brighten my day.” Based on your relationship with your crush, you can also try something more playful or personalized! Here are some more recommended texts for your crush:

  • “Hey, this is me making the first move…your turn! 😂”
  • “Have you thought about me at all today? Type ‘Y’ for yes.”
  • “What are you doing tonight? Because I’d love to be a part of it.”
  • “I feel like our last conversation deserves a sequel.”
  • “Seeing a text from you pop up gives me an instant serotonin boost 😁”
Section 1 of 8:

Good Conversation Starters for Your Crush

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  1. Whether you’ve met your crush in person or on a dating app, you’ll want to start things on a positive note! If you’ve met online, 49% of our readers recommend starting a conversation by referencing something specific on their profile. E.g., if they posted a photo with their dog, mention how cute their pup is and ask for their name! Alternatively, 23% of wikiHow readers prefer starting with a genuine compliment—a method approved by dating coach Laura Bilotta, who says that a “compliment can go a long way in showing you’re interested in the other person and building rapport.”[1] Here are some example conversation starters to try:
    • Personalized Messages:
      • “Wow, what a great photo of you hiking at Zion! How long did that trail take?”
      • “I’m also a huge sushi lover 🍣😋 What’s your favorite spot in the city?”
      • “You’re into pickleball? I’ve been wanting to try it! How’d you get into it?”
      • “I noticed you love Maggie Rogers…have you ever seen her live??”
      • “Since you’re clearly an expert…is Pilates worth it?”
      • “I know you’re a bit of a cinephile, and I’m looking for something to watch tonight! Could I pick your brain?”
      • “I still have a smile on my face from when we were talking about [...].”
    • Compliments:
      • “You have an incredible sense of humor.”
      • “I love your smile!”
      • “I love how passionate you are about [...].”
      • “That color looks incredible on you!”
      • “That jacket looks amazing on you.”
      • “Dang, your confidence is incredibly attractive.”
      • “You’re the definition of a green flag—genuinely!”
      • “Wow, you’ve achieved so much in life! I’m super impressed!”
      • “Your bio made me laugh out loud 😆”
      • “You have such great style!”
      • “Your positive energy is so contagious! I really like that about you.”
      • “You seem like you’ve traveled a TON, that’s so cool and brave!”
      • “Omg I love that photo of you ziplining. I’ve always wanted to try that!”
      • “I see you’re a Tyler the Creator fan…so you must have amazing taste!!”
      • “Wow, your eyes are so beautiful.”
    • Low-Stakes Questions & Recommendations: If the above options don’t appeal to you, 18% of our readers prefer to ask a question, like asking for a recommendation or offering a fun “Would You Rather” question. Here are some examples:
      • “What’s your go-to place for Italian? I’m craving it!” (This text is suggested by communication therapist Rebecca Tenzer, MAT, MA.)[2]
      • “What shows are you watching these days? I need new material,” is an additional example offered by Tenzer.[3]
      • “What’s on your top travel list? I’m making mine and need ideas.” Another Tenzer suggestion![4]
      • “Would you rather have to pass out at 9:30 p.m. or 3:30 a.m. every night (no in-between)?”
      • “Would you rather be brought back as a dog or as a cat in your next life?”
      • “Would you rather have breakfast for dinner or dinner for breakfast?”
      • “Would you rather travel only by train or only by boat?”
      • “Would you rather sing well and dance poorly or sing poorly and dance well?”
      • “Would you rather give up coffee or give up pizza for a year?”
      • “Would you rather have a pool in your backyard or live next to the ocean?”
      • “Would you rather swim with eels or sleep in a bat-filled cave?”
      • “Would you rather be the smartest or the funniest person in the room?”
      • “Would you rather go to a trivia night or go to a standup show?”
      • “Would you rather watch the sunset or the sunrise?”

    Meet the wikiHow Experts

    Laura Bilotta is a relationship coach, dating coach, matchmaker, and the founder of Single in the City, a Toronto-area dating and relationship coaching service.

    Rebecca Tenzer, MAT, MA, is a communication therapist and adjunct professor who specializes in the treatment of depression, anxiety, panic, trauma, grief, and interpersonal relationships.

    Cher Gopman is a dating coach and the founder of NYC Wingwoman LLC, a date coaching service based in New York City.

    John Keegan is a dating and relationships coach with over 15 years of experience in helping people find and maintain romantic relationships.

    Cristina Morara is a professional matchmaker, dating coach, and relationship expert, as well as the founder of a luxury matchmaking service in Los Angeles.

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Section 2 of 8:

Flirty Texts to Send Your Crush

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  1. I mean, if you’re crushing on someone, there’s no better time for flirting—in fact, 38% of our readers like to woo their crush with a playful or flirtatious comment! However, sending a flirty text can be tricky, which is why we also asked our readers for their tips on what actually works. In response, 30% of readers shared that expressing a genuine interest in getting to know the person is the most effective approach, while 28% like to use light-hearted questions to make their crush smile. Here are some more flirtatious, playful, and light-hearted texts to send to your crush:
    • “Just the thought of you brings a smile to my face!”
    • “You seem hot, but I think we should get closer to make sure 😏”
    • “I love how passionate you are about your job. It’s so attractive 💋”
    • “You feel like someone I’d accidentally stay up too late talking to.”
    • “I can’t decide what I want more: food or you.”
    • “Life without you is like a broken pencil…pointless ✏️”
    • “I feel like our last conversation deserves a sequel.”
    • “I feel like we’d have dangerously good chemistry 😈”
    • “I’d rearrange my entire morning routine just to see you again.”
    • “If being sexy was a crime, you’d be guilty as charged 🦹”
    • “I still have your hoodie, so you’re gonna have to come get it soon…”
    • “Call me a thief because I want to steal your heart 🥷🏻”
    • “What’s something non-physical that you find attractive?”
    • “Miss you? Who said anything about me missing you? 😉”
    • “Was that an earthquake, or was it just you rocking my world? 🫨”
    • “Stop looking so cute in the pics you post. You're killing me over here!”
    • “That classic charm won’t work on me. You’ll have to try something else 👀”
    • “Real question: Do you get approached by people all the time? Because you’re really, really cute.”
    • “What are you doing tonight? Because I’d love to be a part of it.”
    • “If I saved your contact name with some emojis, which ones should they be?”
    • “Do you think we’d make a cute couple? 👀”
    • “Soooo…what do your friends know about me?”
    • “If you were in a relationship right now, who would your celebrity hall pass be?”
    • “So I already got your number, what’s next? 😜”
    • “I checked CoStar today, and it said I should flirt with someone stunning. So, how’s your day going, gorgeous?”
    • “If we were a couple in one of those romance books you love to read, would we be friends-to-lovers or enemies-to-lovers?”
    • “What am I up to? Just thinking about how cute you looked the last time we hung out…,” suggests Bilotta.[5]
    • For something more forward, Tenzer recommends a text like, “That blue shirt you wore on your trip to Cabo looked so good with your eyes 😍”[6]
Section 3 of 8:

Deep Texts to Send Your Crush

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  1. It can be hard to really open up to a new person, but 21% of our readers actually said that sharing personal stories is an important way to foster intimacy, while 13% said that sharing vulnerable thoughts is also key. Similarly, given that blossoming relationships are a two-way street, 31% of our readers emphasized the importance of showing genuine interest in your crush’s beliefs and values in order to build a deeper bond. Overall, being observant about what your crush is into and sharing your genuine thoughts and values are truly winning strategies….and here are some example messages to help you do those things:
    • “You’re there, and I’m here. One of us is in the wrong place ♥️”[7]
    • “What motivates you to work hard?”
    • “Would you rather vacation in Mexico or Alaska, and why?”
    • “What’s the best gift you’ve ever been given?”
    • “If you could choose to do anything for a day, what would it be?”
    • “What would you do if you won the lottery?”
    • “Who’s your favorite author?”
    • “What’s your biggest complaint about your job?”
    • “Who in your life makes you laugh the most?”
    • “If you could have dinner with any four people, alive or dead, who would they be?”
    • “If you could go back and time and change one thing, what would it be?”
    • “I just ran into someone SO random today…any guesses as to who it was?”
    • “I’ve always loved gardening, it’s definitely one of my fave ways to spend a weekend!”
    • “I’ve had an intense hyperfixation with R&B music lately. It’s been great for the gym!”
    • “I’m actually pretty competitive when it comes to board games 😬 Just warning you in case you ever invite me to game night!!”
    • “I’m actually a real hopeless romantic, so I’m really looking forward to wedding season 😊”
    • “I’m trying to be productive, but I can’t stop thinking about going to that new Thai place this weekend!”
    • “My day was kinda crazy, but I finally got to just sit down and read this really great new book. How’s your night going?”
    • “I just finished this podcast and it totally changed how I look at gossip. Have you ever listened to it?”
    • “Something I’ve been thinking about a lot lately is how important spontaneity and flexibility is to me.”
    • “I actually just got a major promotion at work, so feeling pretty proud at the moment!”
    EXPERT TIP
    Laura Bilotta

    Laura Bilotta

    Dating Coach
    Laura Bilotta is a Dating Coach, Matchmaker, and the Founder of Single in the City, her dating and relationship coaching service based in Toronto, Ontario, Canada. With over 18 years of experience, she focuses on helping singles date more intentionally, encouraging them to let go of negative patterns so that they can attract the love that they deserve. Her experience, skills, and insights have led to thousands of successfully united over 65,000 singles through events and one-on-one matchmaking coaching sessions. She has been the host of The Dating and Relationship Show on Global News Radio 640 Toronto (AM640) for 6 years and is known as The Hookup Queen of Clubhouse; her popular singles club, Single in the City, has over 95.5K members who regularly join in weekly dating and relationship-focused rooms.
    Laura Bilotta
    Laura Bilotta
    Dating Coach

    Share something about yourself. This can show that you’re willing to be vulnerable and help build a sense of connection. Say something like, “Just finished a great workout at the gym—I’m feeling energized!” or “I’ve been trying to learn how to cook the perfect steak—any tips?”

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Section 4 of 8:

Cute Texts to Send Your Crush

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  1. A cute text is lighthearted but still genuine, making it the perfect fit for someone you have your eye on. When writing a flirty, sweet text message, dating coach Cher Gopman says to “use a little bit of an emoji to show that it’s lighthearted and fun,” but not to “overuse them, because that can come off as too eager.”[8] Here are some cute example texts to get you started:
    • “Have you thought about me at all today? Type ‘Y’ for yes.”
    • “Lunch was super fun! I love sitting across from you :)”
    • “You. Me. Dinner. Let’s go.”
    • “I gotta be honest…your little hair twirl in one of my favorite things that you do.”
    • “I’m in bed and soooo cold…I need a cuddle buddy 🥺”
    • “You’re the WORLD champ of making me smile like an idiot.”
    • “Is it too forward to come out and say that I like you?”
    • “Wanna hear a secret? Okay…I think you’re super cute 🫣”
    • “You looked really cute yesterday.”
    • “You’re my favorite notification!”
    • “Plzzzz stop being so cute. I’m actually trying to focus on something else today!”
    • “I couldn’t wait the ‘three days,’ so here I am texting you now 😬”
    • “Seeing a text from you pop up gives me an instant serotonin boost 😁”
    • “Suddenly thinking about how sweet and kind you are…💛”
    • “I hate everyone…except for you.”
    • “My day isn’t complete without texting you!”
    • “We just said bye but I miss you already.”
    • “I just started reading your favorite book and OMG it’s sooo good!”
    • “You may be out of sight 👀 but you’re never out of my mind 🧠”
    • “I’m still wearing that smile you gave me!”
    • “Your smile is LITERAL magic ✨”
    • “Are you free to call? I want to hear your voice!”
    • “What’s your favorite film? Let’s watch it tonight.”
    • “I think I miss you…maybe too much 😬”
    • “This video just popped up and I thought you’d like it 😗”
    • “I just heard a song that totally reminded me of you!”
    • “I just know you’re going to find this meme absolutely hilarious 😂”
    • “I was just thinking about how well you played in yesterday’s game. You were awesome!”
    • “I’m trying to be productive, but I literally can’t stop thinking of you.”
    • “Ugh, school just wasn’t the same today without you here. You totally miss me too, right?”
    • “Just realized that I never properly thanked you for helping me last weekend. Next coffee is on me!”
    • “You know our text thread is pinned at the top of my messages? So you’re always the first person I think of when I write a text 💗”
Section 5 of 8:

Funny Texts to Send Your Crush

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  1. Consider sliding in with a witty (not creepy!) one-liner, or even “an image or video that you found on YouTube,” recommends dating coach John Keegan. A meme, GIF, or “anything light and fun that kind of moves you from being friends to lovers” is a great place to start.[9] Otherwise, here are some cute and funny texts to send to your crush:
    • “I’ve been meaning to date a [insert your crush’s name], so this must be fate!”
    • “I have psychic powers, and I’m being compelled to ask you out!”
    • “Tell me your biggest regret…mine is not climbing over the table to kiss you last night.”
    • “Ohhh so is this what butterflies feel like? 🙃interesting.”
    • “If you were a vegetable, you’d be a cutecumber 🥒”
    • “Hey, this is me making the first move…your turn! 😂”
    • “I’m not flirting! Just being extra friendly to someone who is extra attractive.”
    • “I’m not a scientist, but I think we would have reallyyyyyy great chemistry 😉”
    • “Quick! What’s something I can text you right now to make you fall in love with me?”
    • “Guess what’s on the menu today? Me-n-u 😋”
    • “Hey! Stop thinking about me so much!”
    • “Thinking of you. And not just because work is slow 🙃”
    • “Guess what I’m so not wearing right now? (It’s socks)”
    • “How have you gone so long without texting me?? I’m such a delight! 🤪”
    • “Can I call you Chapstick? Because you’re da balm!!”
    • “Does a straw have one hole or two?”
    • “I’d take you to a movie, but they don’t let you bring your own snacks!”
    • “I called 911…you’re under arrest for being too cute!”
    • “If you were a fruit, you’d be a fineapple! 🍍”
    • “What do you call 2 birds in love? Tweet-hearts 🐣🩷”
    • “I’m not that great at flirting…could I practice on you?”
    • “Hey, I just met you. And this is crazy…”
    • “Did you really think you could win me over with that cute smile??”
    • “Are you French? Because Eiffel for you 🥐”
    • “Is your license suspended? Because you’re driving me crazy!”
    • “Do you fish? Because I’m totally hooked 🎣”
    • “Are you a banana? Because I find you a-peeling! 🍌”
    • “Thinking about you the way my dog thinks about peanut butter.”
    • “Are you a dictionary? Cause you add meaning to my life 🤗”
    • “My feet are cold. Must be because you knocked my socks off!!”
    • “What’s the most realistic animal sound you can make? 🐄🐅🐘🐒”
    • “Are you a loan? ‘Cause you’ve got my interest. 😇💵”
    • “I need to ask you a very deep, serious question, and your answer will have serious consequences for us both…big spoon or little spoon?”
    • “Whenever I smile, just know it’s because I’m thinking of you and that time you fell asleep at work LOL.”
    • “Thinking of you makes me forget about everything else. So if I fail this test, it’s your fault!!”
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Section 6 of 8:

“Good Morning” Texts to Send Your Crush

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  1. Your “good morning” message can be sweet, flirty, or funny, and you can even ease into the conversation with “a photo of wherever you are,” or say you were getting ready and “a song came on and reminded you of the person,” says Gopman.[10] Here are some other examples of excellent “good morning” messages for your crush:
    • “Good morning sleepy head! I hope you have the best day.”
    • “Wishing you a peaceful morning and a fulfilling day!”
    • “I hope you start your day feeling as awesome as I think you are.”
    • “Have a beautiful morning! I’m thinking of you!”
    • “Good morning! How did you sleep?”
    • “Do you believe in love at first ‘good morning’ text?”
    • “Wake up, sleeping beauty!”
    • “Do you know why the sun rises every morning? Just to see your beautiful smile!”
    • “Morning! I can’t wait to see you!”
    • “Good morning, cutie! Did I make an appearance in your dreams?”
    • “Wake up, princess!”
    • “Hoping your morning is as radiant as you are ☀️”
    • “Good morning! How do you take your coffee?”
    • “You’re my sunshine 🌻 on a cloudy day ☁️”
    • “Morning! I wish I was there to hit the snooze button for you!”
    • “Wakey wakey eggs and bakey!”
    • “Good morning starshine! The Earth says hello!”
    • “Are you tired? Cuz you’ve been running through my mind all night 🏃”
    • “Roses are red, violets are blue, the only thing sweeter than sleep is you!”
    • “If you were here, I’d make you whatever breakfast you wanted (as long as it was a bowl of cereal).”
    • “Good morning! Just wanted to remind you how much you are thought of and appreciated.”
    • “I just woke up to the most beautiful sunrise, and thought you’d appreciate it also 😇 Good morning!”
    • “Morning!! I just heard this song on my commute to work and it reminded me of you—hope you like it!”
    • “Good morning, sunshine! I would never play hide and seek with you, because someone like you is impossible to find!”
Section 7 of 8:

Asking Out Your Crush

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  1. Confessing your love to your crush can be super scary! To help you out, we asked wikiHow readers about the best things to text when you’re ready to level up a relationship: 35% of them said, “Been thinking about you nonstop,” while 28% recommended a simple “Miss you,” and 23% preferred a direct text like “Thinking about your kisses.” So you have loads of options! However, an overwhelming majority of our readers (76% to be exact) shared that it’s better to ask someone out in person over text, so you may want to keep that in mind. But, if you’d still like to ask in a low-pressure text, try one of these expert suggestions:
    • Dating coach Cristina Morara recommends leading with something your crush is interested in, e.g., “Hey, there’s this really cool vegan restaurant that just opened up. I’d love to take you there! Would you like to go on Friday night, seven o’clock?”[11]
    • Similarly, dating and relationship coach Christina Jay, NLP, recommends a direct message like: “I think we have a lot in common. Would you like to go out for dinner on Saturday? I’d really like to meet you in person.”[12]
    • Or, try dating coach Connell Barrett’s example text: “Wow, I’ve really enjoyed our messaging. You’re funny, and you love Bill Murray movies just like me! Let’s have a drink—what’s your number?”[13]
    • And, here are some more example texts to try:
      • “Super last minute, but I’m actually going to be in your area later tonight. Wanna grab a quick drink? No pressure!”
      • “I studied Art, too! Did you see there’s a new exhibition at the museum? Want to check it out with me sometime?”
      • “Hey, I think you’re really special. Are you free for a drink sometime?”
      • “Okayyy, I’m just gonna put this out there. I like you a lot. Want to grab coffee this weekend?”
      • “I lucked out and just got tickets to Maren Morris this weekend. Aren’t you also into country music? Want to go with me?”
      • “I’ve really enjoyed getting to know you better 😊 Would you be interested in grabbing dinner later next week?”
      • “My friend is getting married next month, and I’d love to have you come as my date if you’re interested :)”
      • “You seem to be really great at bowling! Care to give me some pointers in person sometime?”
      • “I’m just gonna come out and say it—I like your vibe. Want to meet up for a drink?”
      • “Hey, getting to know you has been great, and I’d like to see where this goes. Maybe over coffee this weekend?”
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Section 8 of 8:

When & How Often to Text Your Crush

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  1. How often you should text your crush really depends on the situation—like how well you know each other, how you met, and how often they’re texting you! That being said, we can tell you that most of our readers don’t play hard to get or play “games” while texting. In fact, 44% of surveyed readers respond within a few minutes, and 30% respond right away (or whenever they first see the text). If you want a strict rule, however, we’d suggest initiating a text thread with your crush about 2-3 times a week, although you can totally do more if they’re texting you as much as you’re texting them!
    • “It’s all about matching their energy,” says dating coach Jaskaran Singh. “If you’re the one who’s always initiating conversations and they hardly do it, you may want to stop.”[14]
    • Similarly, adds dating expert Kristina Mirgorodskaya, “if your crush doesn’t respond after two texts, give them some space and let the ball be in their court…Any more than 1 follow-up may make you seem desperate or it may annoy the other person.”[15]
    • However, if you’re looking to keep the conversation flowing, 25% of our readers suggest texting open-ended questions…as long as you haven’t already texted multiple times with no response.
    • And what should you do if your crush isn’t responding? When you believe you might be encountering a ~ghost~ or a non-responder, heed the advice of 72% of our surveyed readers: give it time or move on, rather than being confrontational. If they wanted to, they would!
    EXPERT TIP
    Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP

    Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP

    Clinical Therapist & Adjunct Professor
    Rebecca Tenzer is the owner and head clinician at Astute Counseling Services, a private counseling practice in Chicago, Illinois. With over 18 years of clinical and educational experience in the field of mental health, Rebecca specializes in the treatment of depression, anxiety, panic, trauma, grief, interpersonal relationships using a combination of Cognitive Behavioral therapy, Psychodynamic therapy, and other evidence-based practices. Rebecca holds a Bachelor of Arts (BA) in Sociology and Anthropology from DePauw University, a Master in Teaching (MAT) from Dominican University, and a Master of Social Work (MSW) from the University of Chicago. Rebecca has served as a member of the AmeriCorps and is also a Professor of Psychology at the collegiate level. Rebecca is trained as a Cognitive Behavioral Therapist (CBT), a Certified Clinical Trauma Professional (CCTP), a Certified Grief Counseling Specialist (CGCS), a Clinical Anxiety Treatment Professional (CCATP), and a Certified Compassion Fatigue Professional (CCFP). Rebecca is also a member of the Cognitive Behavioral Therapy Society of America and The National Association of Social Workers.
    Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP
    Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP
    Clinical Therapist & Adjunct Professor

    When you’re first trying to catch a guy’s attention, less is often more. So don’t overthink it! Coming on too strong can feel overwhelming or give off the wrong impression, but being too distant may mean they never notice your interest. Balance is key! Be subtle, keep it light, and let curiosity do its work.

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References

  1. Laura Bilotta. Dating Coach. Expert Interview
  2. Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP. Communication Therapist. Expert Interview
  3. Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP. Communication Therapist. Expert Interview
  4. Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP. Communication Therapist. Expert Interview
  5. Laura Bilotta. Dating Coach. Expert Interview
  6. Rebecca Tenzer, MAT, MA, LCSW, CCTP, CGCS, CCATP, CCFP. Communication Therapist. Expert Interview
  7. https://www.betterhelp.com/advice/love/5-love-messages-that-work/
  8. Cher Gopman. Dating Coach. Expert Interview
  9. John Keegan. Dating Coach. Expert Interview

About This Article

Laura Bilotta
Co-authored by:
Dating Coach
This article was co-authored by Laura Bilotta and by wikiHow staff writer, Sophie Burkholder, BA. Laura Bilotta is a Dating Coach, Matchmaker, and the Founder of Single in the City, her dating and relationship coaching service based in Toronto, Ontario, Canada. With over 18 years of experience, she focuses on helping singles date more intentionally, encouraging them to let go of negative patterns so that they can attract the love that they deserve. Her experience, skills, and insights have led to thousands of successfully united over 65,000 singles through events and one-on-one matchmaking coaching sessions. She has been the host of The Dating and Relationship Show on Global News Radio 640 Toronto (AM640) for 6 years and is known as The Hookup Queen of Clubhouse; her popular singles club, Single in the City, has over 95.5K members who regularly join in weekly dating and relationship-focused rooms.
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Co-authors: 4
Updated: February 20, 2026
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Categories: Asking Someone Out | Texting
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