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How to Plan a Perfect First Date

How to Plan a Perfect First Date

Planning that all-important first date can feel like a huge challenge if you’ve never done it before. Where should you go? What should you do together? What should you wear? How can you keep the conversation flowing smoothly? As someone who has planned dozens of first dates over the years, I’m here to share my best tips and advice on how to plan the perfect date when you’re just getting to know someone.

How do you plan a date for the first time?

1. Choose an Activity Both of You Will Enjoy

The most important thing is choosing an activity that you both find fun and engaging. The goal of a first date is to get to know each other better while also having a good time. Try to pick something you’re interested in that you think your date might also like based on what you already know about their interests.

Some low-key first date ideas that allow for conversation include:

  • Going for a walk in the park or at a nature trail
  • Getting coffee or ice cream and strolling around downtown
  • Checking out a new exhibit at a museum or art gallery
  • Catching an afternoon matinee movie
  • Going bowling or mini golfing
  • Having a picnic in the park

Aim to choose something you can both actively do together rather than just passively watching like a movie theater. Interactive activities make it easier to spark conversation when you have different tasks to focus on.

2. Plan Fun Questions to Get to Know Each Other Better

Don’t forget to also plan some questions you want to ask your date to really get to know them on a deeper level beyond just surface small talk. Come up with a variety of open-ended questions to learn about their likes, dislikes, hobbies, childhood memories, career goals, family, values and more.

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Example questions to kick off meaningful conversation include:

  • What drew you to this activity we’re doing?
  • What’s your favorite childhood memory?
  • What things are you passionate about in life?
  • What’s your dream vacation spot?
  • What’s the best or worst first date you’ve ever been on?
  • What are your long-term goals for the next 5 or 10 years?

Have a list of questions ready so you’re not stuck wondering what to say next if there’s ever a lull in the conversation.

3. Dress Comfortably But Put in Some Effort

When planning your outfit for a first date, aim for comfortable but still looking nicely put together. You want your date to feel at ease with you, so don’t over-dress. But you also want to make a good first impression by looking clean and well-presented.

For men, a well-fitted button-up shirt with jeans or chino pants usually works well. Make sure everything is wrinkle-free, your shoes are polished, and your hair and facial hair are neatly trimmed.

For women, a casual sundress, skirt and top, or well-fitted pants with an nice top is always a great option that’s flattering but not too dressy. Pay attention to personal hygiene with a light scent, fresh hair, and minimal but well-applied makeup.

The goal is to look approachable and put-together rather than fancy or trying too hard. Comfort is key when you’re still feeling each other out.

4. Make Wise Transportation Choices

Thoughtfully planning how you and your date will get to and from your activity is also important for saving time and reducing stress. Here are some transportation best practices for a first date: If meeting somewhere public, choose a neutral location neither of you has to travel too far to reach

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Offer to pick your date up so they feel comfortable, but allow them the option to drive separately too. Have backup public transportation details, like bus or train schedules, in case driving doesn’t work out

Save parking nightmares by choosing an activity that doesn’t require hunting for a spot. Consider rideshares as a reliable alternative to driving if there will be alcohol involved

Your goal is a smooth pickup and dropoff experience so your date feels cared for and at ease throughout the outing. Transporting yourselves responsibly can set a great tone.

5. Make Backup Plans Just in Case

As with any social plans, there’s always a chance unexpected scheduling conflicts could arise on the day of your date, even just minor delays. To avoid panic or awkwardness, have some backup plans ready to smoothly pivot if needed.

For example, decide on alternative activities you could quickly suggest, like: Grabbing coffee instead of dinner if one person runs late; Choosing a rain date activity if bad weather threatens outdoor plans.

Having a list of nearby cafes or parks in case one location is too crowded; and/or Deciding a rain check situation respectfully if an emergency pops up.

Being organized with an Plan B already in place allows you both to relax and enjoy yourselves rather than stressing over logistics. It shows you’re a considerate dater focused on comfort and chemistry rather than rigidly sticking to plans.

6. Follow Up After to Set the Right Tone

Beyond nailing the in-person experience, how you follow up after a first date can have a big impact on whether a second one happens. Be sure to: Express genuine thanks for their time and any specific highlights you enjoyed.

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Reiterate you had a great time getting acquainted and would love to see them again; Suggest a potential activity for a second date within the next week or so; Keep all communication positive, respectful and focused on your interest in learning more; Respond promptly but avoid clingy repeated follow-ups if they don’t get back quickly

Proper follow through with a gracious yet optimistic message leaves a good impression as you continue building early rapport. It sets the right tone as friends or possible partners.

Wrapping Up

In the end, the most important factors on any date are letting fun flow naturally and keeping relaxed comfort as the priority. With thoughtfully planned details and a sincere interest in learning about each other, first dates have a way of unfolding smoothly on their own as long as both people simply aim to enjoy themselves. Get out of your head, have questions ready, but most of all – stay present in the nice company and see where the evening leads!

I hope these tips help you feel well prepared to knock your next first date out of the park. Please let me know if you have any other questions. Remember – a little planning goes a long way, but allow things to unfold naturally too. You’ve got this!


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