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Congrats on successfully charming someone into going on a date with you! That’s a huge accomplishment by itself, but now you’ve got to show them a great time to get past that first date—what’s a guy to do? With the proper planning, conversation skills, and followup, chances are you’ll sail through your first date and have a second one lined up before you know it. That’s why we’ve consulted dating experts and put together a handy guide to everything a man needs to know and do to ace their first date. If you’re ready to impress, keep scrolling!

This article is based on an interview with our dating coach and matchmaker, Stefanie Safran, owner of Stef in the City. Check out the full interview here.

Things You Should Know

  • Take time to calm your nerves, look your best, and get in a positive headspace. When you're comfortable, your date is comfortable too.
  • Make your date feel at ease—give them compliments, ask them about themselves, and avoid dominating the conversation.
  • Read your date’s cues about whether a kiss at the end of the date is appropriate. Go for a hug if you’re not sure.

Part 1
Part 1 of 3:
Before the Date

  1. 1
    Choose a casual location or activity where you can talk comfortably. Rather than just sitting and having a cocktail or dinner, grab coffee and go for a walk in an interesting neighborhood or check out a museum. Find natural conversation starters from what you notice around you and have fun with what you’re doing.
    • Try outdoor places like parks, botanic gardens, or zoos. You can walk, sit and talk, or comment on what’s happening around you to avoid awkward silences.
    • Choose places that play to your strengths. For example, don’t suggest happy hour on Thursday if you don’t drink and work makes you crabby.
    • First dates are just as much about having fun as they are about getting to know each other. Go somewhere you enjoy to show your date the best time.
  2. 2
    Give your date specific suggestions so the planning isn’t on them. Avoid generic planning questions like "What do you want to do?" or "When do you want to meet?" Instead, give your date specific location, date, or activity options—the variety shows you’re thoughtful and it takes planning pressure off of them. Try:
    • "Do you want to meet up at the new wine bar downtown tomorrow evening?"
    • "Would you prefer a walk through the park or a visit to the art museum?"
    • "How about we grab a drink Thursday night? Is that a good time for you?"
  3. 3
    Confirm that the date is still on a few hours beforehand. Send your date a short text asking if they’re still available to firm up your plans for the night. It shows you’re considerate and you respect their time. If they’re no longer free, you get the chance to ask them out all over again and show how much you want to see them.[1] Try:
    • "Is 7:15 still good for tonight?"
    • "Hey! Still on for dinner?"
    • "Looking forward to tonight! 8pm still works, right?"
  4. 4
    Refresh yourself on what your date has already shared with you. Learn as much about them as you can from their dating app profile or from the friend who set you up. Scroll through your previous conversations, too. The more info you have about them and their interests, the more you’ll have to talk about on the date.[2]
    • Try not to cyberstalk or Google the person to find out things they haven’t told you. It’ll come off as intrusive or strange.
    • Say things like "I saw in your profile…" or "Stacy mentioned that you…" to reassure your date that your information comes from logical places.
  5. 5
    Put on a clean, sharp outfit that’s appropriate for the location or activity. Dressing for a first date doesn’t have to be complicated—throw on a cool pair of jeans, a washed button-down shirt, and maybe a leather jacket for a polished, classic first date look. Ties and blazers are outdated and a little overkill unless you’re going to a fancy place or you were invited to a plus-one at an event.
    • Dress up enough to look like you’re going somewhere special versus out for a casual night with your buddies.
    • When in doubt, keep it simple but elevated. Wear clean, unwrinkled clothes that fit you well and make you feel confident!
  6. 6
    Make sure you’re well-groomed and looking fresh. Men sometimes underestimate how impactful good hygiene and grooming are to their dates. Shave your face or trim your beard beforehand, clean under your fingernails, and style your hair. Consider booking an appointment with a stylist for a new, clean look.
    • Go easy when you apply cologne—it usually smells stronger to others than it does to you.
    • Be consistent with your grooming habits. Compliments about your appearance from coworkers or friends can boost your confidence before the big date!
  7. 7
    Calm your nerves with exercise, your grooming routine, or self-care. Exercise earlier in the day to relieve stress and work out your nervous energy. Take your time getting ready and do a mental walk-through of the date to picture yourself having a great time. Read some fiction to clear your mind and perk up your short-term social skills and emotional intelligence.[3]
    • Do whatever you like or need to do to get in a good headspace. If you’re comfortable before the date, you’ll make your date feel comfortable too.
  8. 8
    Get rid of the idea of "the perfect match." It’s easy to project your hopes and desires for a fulfilled love life onto a new person. When you catch yourself fantasizing before the date, stop yourself and focus back on the present moment. Remind yourself to see your date for who they really are to keep your projections from growing and growing.
    • Be mindful of how much fantasy you’re projecting. Optimism is good, but putting all your hopes on one person can lead to a disappointing outcome.
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Part 2
Part 2 of 3:
During the Date

  1. 1
    Be on time (or even a few minutes early). Plan to arrive at the park, coffee shop, or bar a few minutes early so your date won’t have to wonder where you are if they beat you.[4] Use the time to make sure your table or activity is ready, or find a backup plan in case the bar is too crowded or the coffee shop is unexpectedly closed.[5]
    • If you’re picking up and driving your date, aim to be right on time. Being early might be just as inconvenient as being late.
  2. 2
    Focus on making your date feel comfortable. Remember, they’re probably just as nervous as you! Offer a quick compliment as an ice breaker and make them feel good right away. Offer to open doors or grab the table to show you’re taking care of things and set a comfortable tone. Your date will use these cues to decide whether they feel OK pursuing you more.
    • If they’re receptive to your efforts, you can try sitting closer to them or touching their hand a little bit. Make sure not to go overboard with touching too soon.
    • Follow your date’s cues to see if they want to be touched, or ask them if it’s OK. When in doubt, skip the touching (especially on a first date).
  3. 3
    Compliment your date honestly and sincerely. Honesty is the best policy when it comes to compliments—if you think somebody has beautiful eyes, it's okay to say it! Keep it genuine and say what you really believe. If you’re complimenting them just to flatter or impress them, it’ll come off as disingenuous.
    • It’s fine to say "You look great!" when you meet, but too many comments about their body can make them feel objectified.
    • Delivering a sincere compliment makes your date feel good and makes you appear more confident and sure of yourself, too.
    • Try some simple but thoughtful compliments like:
      • "You have incredible eyes."
      • "You’re so funny! The time is just flying by."
      • "You’ve got great style. Those earrings are really eye-catching!"
  4. 4
    Reveal information without over-sharing or dominating the chat. Most daters don’t enjoy it when someone tries too hard to impress them and can’t stop talking about their accomplishments. Ask questions and leave your date room to talk—giving them a chance to share will make you appear more interesting and entertaining.
    • If old relationships come up, only give yourself about 30 seconds to explain why it didn’t work out. Otherwise, your date might think you’re stuck on an ex.
    • Focus on getting to know your date well enough to find points of connection or things you have in common to instigate a true, two-way conversation. Try:
      • "I love that movie too! What’s your favorite part?"
      • "I grew up in a rural area but love big city life. What brought you to the city?"
      • "I love that you do volunteer work! That’s something I’m trying to do more of. How did you get started?"
  5. 5
    Look and be interested in what your date has to say. Make eye contact and lean in toward them to show you’re listening and engaged. Keep them talking instead of always bringing the conversation back to you and stay present to see what they want—make sure not to use the exact same questions and stories you pull out for every date and respond genuinely to what your date is saying.
    • Put your phone away so you’re not distracted. If you have it out, turn off your dating app notifications (yes, even if you met your date on an app).[6]
  6. 6
    Expand on details and let the conversation flow naturally. Try not to skip superficially from topic to topic—instead, dig deeper into something your date said with open-ended questions to spark a really great conversation. For example, if they say they’re from Detroit, ask them what it was like living there, what they enjoyed doing, and why they moved to really get to know (and charm) them.
    • Try not to ask yes or no questions like "Do you have siblings?" or "Do you like pizza?" They lead to shallower answers than open-ended questions.
  7. 7
    Decide who’s paying before the check arrives. If you plan on paying, mention it when you ask your date out—say something like "Drinks on Friday? My treat." so it’s clear from the beginning. If your date offers to pay in the moment, smile and tell them "It’s my pleasure."[7]
    • Alternatively, tell your date they can get the next round if they’re insistent. Splitting the bill is perfectly common and acceptable too.
    • Avoid Venmo requesting money from your date while you’re still together if you’re splitting the bill. It’ll make you seem uptight about money.[8]
  8. 8
    Keep the date short and sweet. If possible, keep it about an hour long. If there’s amazing chemistry and it goes longer, that’s great! But remember that the point of a first date is just to meet each other and decide whether you’re interested in seeing each other again.
    • A shorter date also makes it easier for you to leave in case it’s not going well or you discover you’re not super interested in your date.
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Part 3
Part 3 of 3:
After the Date

  1. 1
    Try to solidify plans for a second date before you part ways. Say something like "I’d love to see you again" or "Maybe next time we can check out that restaurant you mentioned" to let them know you enjoyed your time with them. Then, create a plan for the second date and schedule it as soon as possible to keep things rolling. Try:
    • "How about we check out that new exhibition on Thursday?"
    • "I’d love to meet up with you again. How about Sunday?"
    • "I definitely want to see that speakeasy you mentioned. Maybe we could go this weekend."
  2. 2
    Read your date’s cues about whether they want a goodbye kiss or not. Consider whether a kiss is appropriate based on your chemistry and the way they respond to your flirting or touching. There’s no hard rule about whether a kiss is a good idea or not—it all depends on what your date is feeling. When in doubt, skip the kiss and go for a quick hug instead. It’s also 100% OK (and thoughtful) just to ask them if they’d like a goodbye kiss.
    • Signs that your date wants a kiss could include lingering eye contact, light touching, flirting, softening their voice, or complimenting your lips or mouth.
    • If you met online, chances are your date won’t want a kiss after just one date. If you knew each other before the date, they may be more open to it.
    • Avoid handshakes if you like the person. A handshake makes the date seem like more of a business meeting than a fun time together.
    • Many people (especially women) feel uncomfortable with a kiss until they get to know you better. It might take up to 3 dates before it feels right.
  3. 3
    End the night without a hookup to leave your date wanting more. Walking your date home is a nice gesture, but say your goodbyes and leave without putting pressure on them to let you inside or to hook up. Lingering in the hopes of getting lucky can seem desperate or uncomfortable.[9]
    • Consider declining an offer to come inside if they ask. It makes you seem polite and gentlemanly, and the anticipation for next time creates romantic sparks.[10]
  4. 4
    Reach out to your date again quickly. Forget the "wait 3 days to talk to them" rule—if you had a great time and you like the person, put yourself out there and talk to them. There’s no "game" to play or a set amount of time you have to wait. It’s more honest to just talk to them when you want to.
    • In the early stages of getting to know someone, it’s better and more personal to give them a call rather than to text them.
  5. 5
    Follow up with your date if you said you’d communicate with them soon. When you tell someone you’ll call, make sure you really do it—you’ll lose points if you forget or if you wait too long and use the "I got really busy" excuse. Consistent and quick communication is a big factor in getting them to want to see you again.
    • Watch your social media—if you’re posting a ton but then come up with excuses about why you didn’t call or text, you could be in trouble.
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      • Remember to drink responsibly if there’s alcohol involved in your date. Getting too drunk (or showing up drunk) on a first date is a big red flag and will probably keep you from getting a second date.[11]
      • No matter how the date goes, always aim to be your authentic self. False bravado and ingenuine opinions won’t help you secure a second date or a deep relationship.
      • Don’t be afraid to try for a second date if the first one went poorly. You never know what will happen when you meet again!


      • Remember that consent is crucial for any type of touching or sexual activity. Unless you have a verbal and affirmative expression of consent that was communicated freely and clearly, do not try to escalate things physically.[12]

      About This Article

      Stefanie Safran
      Written by:
      Dating Coach & Matchmaker
      This article was written by Stefanie Safran and by wikiHow staff writer, Dan Hickey. Stefanie Safran is a Dating Coach, Matchmaker, and the Owner of Stef in the City, a Matchmaking and Dating Coaching business focused on an honest and hands on approach. Stefanie labels herself as “Chicago's Introductionista®” as she has over 15 years of experience in the matchmaking industry. Her work has been featured on various media such as: ABC7, NBC5, CBS2, WGN, FOX, The Chicago Tribune, The Chicago Sun Times, The HuffPost, and Refinery29. She holds a MBA in marketing and branding from Loyola University in addition to her BA from the University of Wisconsin-Madison.
      2 votes - 100%
      Co-authors: 4
      Updated: August 22, 2022
      Views: 731
      Thanks to all authors for creating a page that has been read 731 times.

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