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Dating Spotlight: I Had a Great First Date. What Do I Do Now?

My matchmaking and coaching clients come to me with excitement and a little fear, wanting to find their next partner. They focus on presenting themselves on a first date, what to say or not to say, and whether their date will like them. Unfortunately, most people don’t know what to do after a mutually compatible first date. This is when things can start to fall apart if both people do not make a considerable effort to keep things interesting and exciting.

I’m reminded of pregnant women focusing so much on labor and birth instead of reading everything they can on childhood development, raising children to be emotionally mature, and how to meet their own needs while parenting. There is so much more to come after the labor and birth, and many parents are surprised at how little they know about the FOREVER PROCESS of having a family.

Let me paint you a picture of what a great first date looks like:

Butterflies dance around in your belly. You are five minutes early, so you go to the restroom to wash your hands, hoping the nervous energy you are feeling gets washed down the drain. Walking back to the entrance, you see a person looking around that seems as awkward as you feel right now. You take a deep breath, confidently walk up to the person, and smile. They ask if you are “insert name here,” and you both take your seats and proceed to have a fabulous night.

There is laughter, deep sharing, warmth, and a bit of raw, unfiltered communication. You both discover similarities and shared experiences in your past. You bond over food, your childhoods, and your favorite music. Then you find yourself imagining what they are like with their friends, on vacation, and at their job. You try to keep it in the moment and not overwhelm them with questions. You don’t want this date to seem like an interview, even though there is so much more you want to know about them.

The next day you both send feedback to the Matchmaker. You are delighted to discover the great news that you both like each other and want to see each other again. The Matchmaker shares phone numbers, so you can both take it from here. OR If you met on an app, one of you texts the next day to say they had a good time.

The Hard Part Comes Next

After a great first date is when the waters can get muddy. One of you must reach out to the other person and spend some vulnerable minutes, hours, or days waiting for a reply.

Does any of this sound familiar?

I know many people who describe this stage as a torturous place of limbo.

  • Will they call?

  • Should you text?

  • Do they really like you, or were they just being polite?

  • Can you see yourself fitting into their life?

  • You focus on all of the potential red flags.

  • You fear being ghosted. Read more here.

Gender roles: Who asks for the 2nd date?

There are no rules that govern who is supposed to reach out to initiate contact after a great first date. It is not right or wrong for a woman or a man to be the first one to text or call. This has more to do with the type of person you are.

  • Is it your default to wait for things to happen, or do you make things happen in your life?

  • Were you raised to believe that the man asks the woman out and the woman waits for the man to ask?

  • Are you a man who is confused about your role with a feminist and independent woman?

  • Are you LGBTQ, and there are no gender roles, so you feel utterly confused about who will initiate contact and when?

Just like I want to smash the patriarchy, I also want to do away with the SHOULDS surrounding who asks the person out on a date. In my opinion, if you want a date with someone, ask them out. If this sounds scary to you, know that it’s difficult for most people regardless of gender. Rejection is the common fear most people have when asking someone out on a first, second, or third date. This fear doesn’t magically disappear if you are a man, by the way.

I hear many of my female clients tell me they want the man to take that next step to show them they are serious about seeing them. I know men who tell me the same thing. So, I wonder why these old rules still apply. I would like to think we now live in a time where equality has entered the dating scene. However, I want to honor what my clients desire in terms of waiting or reaching out after the first date. If I know they want to wait for the other person to initiate contact, I’ll let the other person know as a way to nudge them.

There are many ways to keep the connection going after a fabulous first date:

  • Phone calls – Talking on the telephone is a beautiful way to get close to someone you have just met. Without face-to-face contact, many people can open up more and allow themselves to be vulnerable. You can take your call outside for a long walk and get the benefits of exercise and fresh air at the same time. Discuss books, podcasts, and shows you are interested in. Discuss your plans for travel or future events to gauge their interest in possibly joining you.

  • Texts – Sending the first text can be scary. If you want to increase the odds of getting them to write you back, do not start with “Hi” “How are you?” “Just letting you know this is my number.” Instead, begin your message referring to something they said or did on the date that you found charming. Compliments are an excellent conversation starter. Ask them about a book, movie, or a place they mentioned on the date. Say something random and interesting about your day and ask their opinion on it. BE INTERESTING AND ASK A QUESTION.

  • Video Chat – Schedule a video call and call it a date. This is wonderful for long-distance relationships or when one of you has kids at home, after their bedtime. Play Truth or Dare. Give a house tour. Dance to music. Cook together.

  • Send videos – Video yourself talking to them. Tell them something cool about your day, or ask some questions you’ve been wondering about. When they see your smile and hear your voice, it’s a great reminder of how wonderful you are. Tech Tip: Try to keep it at 60 seconds or less to make sending by text easier.

  • Comment on their social media posts – I recommend not following your first date on social media right away. Instead, allow time to get to know them organically before doing a deep dive into their past. However, once you are connected on social media, liking and commenting on posts is a great way to show them that you are interested in their lives.

  • Long-distance dating – I have experience with this and know it can be exhilarating and very doable to keep the excitement going from afar. Watch episode 8 of Dating Reality Check: The Reality of Long-Distance Relationships for some fabulous suggestions by three of my favorite Matchmaker friends.

Second date ideas

Think beyond dinner and drinks and consider doing an activity together:

  • gallery openings

  • outdoor markets: farmer’s, art, craft, etc.

  • wine tastings

  • live music

  • cooking together

  • dance class

  • hiking

  • exploring botanical gardens

  • making or painting pottery

On the second and third date

Many people consider the second date as an in-person event. However, if the intention is to have a date, but you can’t be physically together, virtual dates and phone calls are excellent stand-ins. The second and third dates can be ideal for diving deeper into topics you are still curious about. First date jitters are likely gone, and the walls have started to come down.

Be more open and vulnerable

If we critique ourselves too much in the “early-days” dates and hide our true selves, we will not know if we are truly compatible. This is when it is more appropriate to bring up sensitive issues. Topics such as discussing religion, your ex, and politics are not advisable on a first date, but there are no rules on a second or third date. However, be aware that these topics can bring up intense feelings, and if you are not ready for this, wait until you feel safe. Watch Brené Brown’s Ted Talk: The Power of Vulnerability (and then read all of her books and listen to her podcasts) for more info on being vulnerable.

I love playing Truth or Dare in the first month of dating someone. You may feel more comfortable asking vulnerable questions when playing a game. Also, Truth or Dare can be really fun on a video chat. You can discuss core values and life goals by carefully selecting questions (or coming up with your own) before the date. See this list for sample questions and dares.

Take a look at 36 questions in love for a fun way to get to know your partner deeper. This site was created to help people fall in love. One question pops up on the screen at a time, and it can be played anywhere. First dates may not be the best time to play this game together, as some questions are intense. But second and third dates are ideal for learning more about their experiences. I once played it with my best friend of 20 years and her husband of 25 years, and we all learned new things about each other.

Introducing your “date/partner/Boo” to friends

When to do this is up to you. I find it helpful to get to know a new person better when I see them interacting with their friends and in large groups. They will likely let down any wall or shell they have when with their friends. And their friends will reveal things about them either directly by telling you of their embarrassing moments and experiences or through storytelling.

“The beginning of every new relationship can be scary, confusing, and tricky. You are not alone or immune to the awkwardness that comes with getting from Point A (great first date) to Point B (a second date and eventually an established relationship). My advice is to enjoy the process of getting to know new people by staying unattached to the outcome. If it fades away, they are not your person. This ending will make room for your next partner." Anastacia Elizabeth Walden

Matchmakers and Relationship/Dating Coaches are a valuable resource if you desire more support.


Anastacia Elizabeth Walden

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

VIP Matchmaker @ Tawkify

Relationship Coach

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