top of page

How to Fall in Love with a Stranger

Whether you are meeting new people on dating apps or from a matchmaker introduction, you are essentially meeting a stranger with the hope of love. As opposed to dating someone you’ve known for years, where you can skip a few steps since you have the background to build upon. There are many ways to sabotage a first date, and I am sure you have a few perfect examples of this from your past or people you know.

Your first date with a stranger is merely an introduction

You may have minimal information before this first meeting, leaving many unanswered questions. Yet, you don’t want to make the common mistake of turning a first date into an interview. Keep your questions to two to three, and be mindful of having a balanced conversation.

The purpose of this first date is to discover if your personalities are compatible. Sharing stories and talking about what is around you is a great way to be in the moment. If the energy between you both feels good, save more questions for the next date. Be okay with not knowing everything so quickly. Allow your curiosity to build.

Laughter is a great icebreaker. I’m not suggesting you laugh at their boring stories or a joke you don’t find funny. But finding and expressing humor and pleasure in a conversation will draw another person towards you.

Wonderful first date ideas

  • Average length: one to two hours

  • Meet for lunch

  • Drinks and appetizers

  • Art gallery opening

  • Food trucks

  • Walk around a big bookstore

  • Picnic in a park – both bring something

  • Walk around botanical gardens

  • Bowling, billiards, foosball

Ways to sabotage a first (or any) date

  • Showing up late without a proper apology

  • Getting drunk

  • Oversharing of personal information

  • Interrupting repeatedly

  • Asking too many questions

  • Not revealing enough about yourself

  • Bragging about your money, career, home, car, etc.

  • Talking too much

  • Stiff body language

  • Being too serious (not laughing is a common complaint I hear from clients after first dates arranged by a matchmaker)

Second date

Reaching the second date stage is a relief. When both people are excited to meet again, there is a level of comfort that allows for more openness. You have passed through the unknown by admitting there is more you both want to discover.

You can now ask more intimate questions about their family, past relationships, childhood, religion, and politics. This is more appropriate on subsequent dates, as opposed to first dates.

Many people are more reserved on the first date, trying to do things right so the other person will like them. I counsel my coaching clients to start being truthful and open on date one instead of playing games. However, many of us have learned defense mechanisms and unconsciously change our behaviors to be friendlier, polite, and uncontroversial when meeting someone new. This wall starts to shed on the second and third dates for most people.

Second date ideas

  • Do any activity together that you both enjoy

  • Walk on the beach or around a lake

  • Axe throwing

  • Mini golf or Top Golf

  • Kayaking or canoeing

  • Enjoy a cup of tea together

  • Painting or pottery class

  • Live music

  • Museum or art gallery

  • Art or wine festival

  • Bookstore or book events

Third Dates

In my experience, dates three through five tell you a lot about a person. This is the time when the walls really start to come down. For those people who have been trying to present the person they want you to know instead of who they indeed are, the jig is up.

Most people cannot keep this facade up for very long. When people feel safe around you, they may have more alcohol, share more personal stories, and their annoying habits may shine through. I love this stage because I find realness, flaws, and vulnerability interesting.

Date # 3-5 is usually when your inner knowing gives you answers about whether you want to continue dating or move your separate ways. If your meet-ups have only involved sharing meals, drinks, or going to the movies, it’s time to do something more adventurous. This will allow both of you to know more about each other.

Ideas for dates #3-5

  • Plan an outdoor adventure together to learn more about their competitive side.

  • A weekend getaway will teach you about their planning skills, sharing, compassion, and ease of communication during a long drive or flight.

  • Get together with their friends to see what the dynamics are.

  • Attend game night at a friend's house or Trivia night at a local bar.

  • Bring them around your friends and listen to their feedback later.

  • Plan a long phone or video chat. Take turns asking deep questions or Esther Perel’s card game Where Should We Begin or play Truth or Dare.

Will it last, or will it end?

If you both make it through five dates (in-person and/or video dates), are still curious to learn more, and want to spend time together, you have a good chance of lasting for months or years.

“If you are both being truthful to each other and yourself, working on respectful communication, and compromising on activities to share, you are leading towards building a foundation of security and connection.”

When to seek Relationship Coaching or Therapy

When you feel triggered, defensive, or unsafe sharing your needs and desires with your partner, this is a great time to speak with a Relationship Coach, a therapist, or a trusting friend to get another person’s perspective. Talk to someone else if you don’t like one person's advice about your situation.

You are ultimately the one who decides whether to stay and work on the relationship or to call it and move on. However, sometimes our past hurt and trauma, childhood experiences, or family dynamics trigger us in a way that isn’t about this new person. Instead, it’s about our past beliefs and self-worth. This is the core of my work with individuals – helping them to recognize where they can grow and encouraging them to discuss their needs and desires with their partner in a healthy way. Empathy can dilute shame and bring a person back to their authentic self.

Everyone deserves a trusting and loving relationship.


Anastacia Elizabeth Walden

Writer, Editor, Author, and CEO @ Walden Writes For Women

Published Books -

Relationship & Empowerment Coach @ Roots Coaching


Click here to read a featured article about Roots Coaching and Walden Writes For Women

123 views0 comments

Recent Posts

See All


Post: Blog2_Post
bottom of page