Break the ice with a friendly greeting.
Catch their interest and get a conversation started. Try something more engaging than a simple "Hey!" or "What's up?" Take a look at their dating site profile and examine their likes, dislikes, and any other information they provide there. Then, tailor your greeting to something on their profile; for example, you could break the ice by asking about a hobby or compliment one of their pictures. "Hey there! I see you're a painter. That's so awesome!!" "Hi! Your profile pic is adorable. I'm curious what kind of puppy you have—they look darling! ????" "Hi there! I saw that you're a basketball fan. Me too! What's your fave team?"
Ask your crush questions.
Getting to know your crush helps you establish trust with them. They're much more likely to say yes if they feel like they know you a bit—and this gives you a chance to woo them before sealing the deal. Ask open-ended questions requiring more than a yes or no answer; your exchanges will last longer, and your crush will see that you're genuinely interested in their lives. "What are the most important things on your bucket list?" "If you could have any superpower, no strings attached, what power would you choose?" "What's something that everyone hates but you love? No judgment here; I'm curious! ????"
Discuss common interests.
Let them get to know you too and find topics you can both talk about. Use your crush's dating profile (and the questions you ask them) to discover mutual interests. This will give you more to talk about as you get to know one another. Once common interests are established, your crush will also feel more connected to you—and likely become open to the idea of a date. "OMG, none of my other friends have read the Lords of the Rings books from cover to cover. I thought it was just me! ???? What'd you think of the movies by comparison?" "It's so cool that you know how to play guitar. I play drums—I'd love to jam together sometime!" "Ooh, a fellow D&D enthusiast! ???? Got any cool stories from your home game to share?"
Exchange phone numbers.
Texting helps you deepen the relationship before meeting in person. Drop a casual request once you've warmed up to one another over the dating site. If you feel it's still too early to ask for a date, but you've spent longer than expected on the chat or had several online conversations, a phone number is the safe next step to take to get closer to this person. "I have to go back to work now, but I enjoyed talking to you. Do you have a phone number so that we can continue our chat later?" "It's been really fun getting to know you! Would you be open to exchanging phone numbers? I'd love to move the conversation over to text. ????" "Hey, I'll be away from the computer today, but I'd really like to keep chatting. Feel free to text me at (555)-555-5555!"
Ask them out after a few messages.
Look for signs that they're interested after 5-10 messages. Many people who use online dating apps score a first date after exchanging between 5 and 10 messages with the person they like. Avoid asking them out right away, but don't leave things hanging on the dating app (or on the text chain) for long either. Signs that your crush returns your feelings include: They match the length of your messages. If you send a 3-sentence message and get a reply around the same length, it's a sign that they're engaged and interested in talking to you. They're asking you lots of questions. Open-ended questions from your crush show that they want to know you just as much as you want to know them. They tack emojis and exclamations into their texts. The more they emote, the more invested they likely are. Emojis are a great way to convey warmth and depth in messages, and exclamation points show enthusiasm. Although this is the hardest part, think of your request as a step that will relieve the tension in the conversation. It will give both the chance to do something together where you can actually get to know each other for what you really are.
Keep your invitation casual.
Ask your crush out in a way that sounds light and fun. Often, if you've been chatting casually on a dating app, it's better not to say the word "date" since that instantly puts pressure on the meeting. Instead, plan an entertaining date and phrase it as "meeting up," "hanging out," or just ask them if they want to do that activity with you. "I feel like you and I have really clicked! Would you want to meet up for dinner and a movie on Saturday?" "I really like talking to you. Why don't we continue our chat at the Mexican restaurant downtown next weekend?"
Work the date into your conversation.
Use the current topic to suggest a date idea. Wait for a natural point in the conversation and suggest an activity based on that, whether you're talking about your mutual love of Italian food or your obsession with amusement parks. That way, you know they'll be interested in whatever date you propose, and it'll feel more natural than a sudden date invitation from out of the blue. "You know, if you like matcha, I know this cafe with the BEST lattes. I'd love to take you there this weekend!" "Speaking of this weekend, I'm free on Sunday, and I've been dying to show you this delicious brunch spot near me." "I agree, Mamma Mia was such a fun movie! Actually, I think the drive-in is playing it one night next week. Wanna go together?"
Use their profile to think of a date idea.
If the date aligns with their interests, your crush will likely say yes. Use the research you've done before the conversation to suggest an activity you might enjoy doing together. For example, if you both like foreign films, find one playing next to you and invite them. Present your suggestion as a way to continue the chat elsewhere. "Since you're such a Disney fan, why don't we watch a few movies this weekend? You can show me your favorites! ????" "I saw you like roller-skating. Would you wanna go to the rink with me on Friday?" "You love painting, right? Let's check out the art museum next week!" Reader Poll: We asked 143 wikiHow readers how they initiate conversations with people online, and 53% said they talk about something on their profile. [Take Poll]
Turn the date into a learning experience.
Ask your crush to teach you something new and exciting. They'll be flattered if you express interest in learning more about one of their passions! Conversely, you could offer to give them a lesson if they seem curious about one of your hobbies. For example, you could invite them over for a baking tutorial or ask them to show you how to knit. It's a great way to bond with one another. "I've never made cheesecake, even though I can't get enough of it. Think you could show me how? Plus, that means we both get cheesecake! ????" "Ooh, ice skating seems fun, but I don't know where to start. Wanna show me the ropes on the rink? ????" Alternatively, suggest doing something brand new for both of you. Invite them to do something they've expressed interest in but never tried before.
Give them a few date activities to choose from.
Appeal to your crush by letting them choose the activity they'd enjoy. When you provide several ideas to choose from, your crush will have more incentive to say "yes," since they're in control and get to tailor the date to their interests. Based on your messaging exchanges, think of a couple of choices you think they'd like and ask them which one they want to do. "So, I thought we could hit up that mini-golf place you mentioned—or maybe check out the aquarium. Would you be interested in either of those? ????" "Hmm. Which do you like better: dinner or brunch? Because I'd love to take you out for one of those this weekend! ????" "I really like talking to you! Would you want to continue the conversation over coffee tomorrow, or maybe take a walk in the park downtown?"
Invite them out with a group.
Hanging out with friends is less intimidating than one-on-one. Assuming you and your crush haven't met in person yet, a group hang puts less pressure on you while making them more comfortable with meeting a stranger for the first time. Suggest that they come and meet you at a bar or some other fun spot where a group can have some fun and let the relationship grow from there. "Would you be interested in bowling with me and some friends this Friday? It'll be a blast!" "I'd love to meet up in person, and I'm going to the zoo with some friends this weekend. Wanna come too?" "You like DC heroes, right? Some friends are going to see Wonder Woman tomorrow, and I'd love it if you came too!"
Make direct and specific plans for your date.
Give your crush a concrete activity, time, and place. This makes the idea of a date seem more real for your crush and not just a vague suggestion. Plus, having specific date ideas in mind right when you ask will prove how interested you are; it shows you've put genuine thought into spending more time with them. Don't worry if they're not free on the day you suggest—just smoothly offer an alternative for them. "You, me, and that cool new arcade bar that just opened. Would you wanna check it out with me on Saturday night?" "I've been dying to see the next Thor movie. Want to go see it on opening night with me? I think it'll be so fun!"
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