Why Are First Dates So Exhausting?

By Amy Nobile Messing, as told to goop

Amy Nobile Messing is a holistic dating coach and founder of her dating service, Love Amy.

First dates can bring up so much anxiety because we think we need to look and be perfect the first time we meet someone. We’ve been conditioned to want to be chosen, so that’s often our goal. This can turn a potentially pleasant event into a debilitating nightmare. But if we shift our thinking around dating—which is what I help people do—it can change how we experience first dates (and the ones that follow).

I see the first date as a “mini-screener date.” That means it should be short (I recommend 45 to 60 minutes), convenient (no more than 15 to 20 minutes away), and give you enough information to see if you want a second date with this person. Prepping helps this process be more effective. Here are some things I recommend.

Determine your core values. I always tell clients to take a step back, and ask “who am I now?” To help figure out what matters to you, take my five-minute core values quiz.

Create one question to ask your date stemming from your core values. This will help to see if your values align. For example, if “gratitude” is a top value for you (this was mine!), you can ask “What are you most grateful for in your life right now?”

Prep your dating outfits ahead of time. I always suggest having two or three go-to first date outfits so that you never stress about what you’re going to wear. It can be casual, like jeans and a cute top or a dress and sneakers—whatever clothes you feel really good in. I suggest keeping them in a specific place in your closet so that they’re easy to find.

Don’t spend time worrying about makeup/hair. A screener date is meant to be casual; no need to wear full makeup or blow out your hair. For example, in my past dating life, I’d go on first dates wearing athleisure, a ponytail, a little mascara, and lip gloss.

Get to your location a little early. I tell my clients to choose a place to meet that they’re comfortable with and to get there 15 to 20 minutes early. You want to give yourself enough time to acclimate to the vibe of the space, relax, and release some nervous tension. While you wait, you can take deep breaths, do a short mediation, journal, chat with the barista—whatever will help you feel calmer and more embodied before your date arrives.

Intentional First Date Talk

It can be awkward when you’re trying to figure out what to say on a first date (hellooo, no one teaches how to intentionally date!), especially when you’re nervous. But having some key questions in mind will help ease the tension and keep the conversation flowing.

First, cut through the small talk. Once you’re both settled in, I suggest starting with a simple question: How’s dating going for you? It puts you on the same team, it’s relatable, and it will give you valuable information—for better or worse—to get to know your date more. Just be prepared to answer the question too.

Ask more questions. As the conversation flows, ask your core values question (and don’t be afraid to say “Okay, I’m pivoting the conversation! So I took this core values quiz…”) And get curious. Don’t be afraid to ask follow-up questions to their responses. For example, if one of your core values is “family” and your date mentions their brother just had a baby, you can say “Wow how amazing! How was that for you to witness?” The key here is to be warm and validating while getting a sense of who this person is.

Be skillfully vulnerable. When getting to know someone, it’s important to strike a balance between being too guarded and oversharing. You want to give someone a sense who you are. Not everything will be appropriate for a first date, but you can dive deeper on subsequent dates.

For example, if someone asks you about your last relationship, you don’t need to share all the gory details on the first date. But you don’t want to be so guarded that you’re not providing some information to show your date who you are. The balance is important because it can determine whether you both agree on seeing each other again. I help clients practice their response to “what was your last relationship about?” Your answer should be no longer than one or two sentences on a first date. When I have a client say to me that they can’t get a second date—they go on many first dates but are never asked on a second—it’s an indicator for me that they are either being too guarded or they are oversharing.

Have a “hard stop.” It’s important to establish boundaries in a relationship—creating a hard stop on the first date is a great place to start. Before your date, let them know how much time you have to chat with them (you can text “I’m excited to meet you on Saturday! Just FYI, I’ll have about an hour before I meet up with friends.”). During the date, when you notice you have about 10 minutes left, kindly let them know that you need to leave soon.

To avoid an awkward exit, after you wrap the conversation (and date) up, I suggest you say, “Okay well I’ll say goodbye here; I’m going to use the restroom. Thank you so much!” This way, you won’t be scrambling to see which direction they’re headed as you both leave at the same time.

What to Do Post-Date

As women we’re often taught that dating is about being chosen—that we need to wait to see if our date likes us and then let them decide if there’s a second date or not, even if we’re not sure if we even like them. I take a different approach that involves consciously reflecting on your date.

Answer post-date questions. I use a post-date worksheet with my clients that helps them discern if they’re actually aligned with dates. Below are some questions that are included in the worksheet to help gauge how you felt physically, emotionally, and mentally throughout the date. I suggest you write your answers in a journal so you can reflect on them throughout your dating journey.

• How did my nervous system feel? Did I feel tension? Was my breathing shallow? Did I feel jittery?
• How did I feel emotionally? Did I enjoy myself? Did I feel giddy, joyful, stressed, heavy?
• Did I have fun? Did I laugh?
• Did they ask me questions? Did they seem genuinely interested in the conversation?
• Did I act like myself around them? Did I feel seen and heard?
• What surprised me about this person?

Use the 4/4 rule. After four dates with someone, I ask my clients to implement the 4/4 rule to determine whether they’re aligned on a higher level. This is the anchor of my dating program because it helps people date with intention: By the end of the fourth date, you need to see alignment with these four pillars to continue dating:

• Are your core values aligned? By asking questions that stem from knowing your core values and what matters to you, you’ll be able to gauge quickly whether you’re a match.
• Is there chemistry? Contrary to popular belief, chemistry often works in reverse, and you can build chemistry over time. You don’t need crazy sparks on the first couple of dates, but you should be able to imagine kissing this person in order to continue.
• Is this person emotionally mature? A key question to ask your date is: “Tell me about your last relationship!” Their response can tell you a lot about their maturity (a major red flag is speaking negatively about their ex).
• Are they ready for the same thing that you’re ready for? This is critical. People will often say they’re ready for a relationship, but they’re really not. A good question to ask is “Let’s time jump—in three years, where are you, what are you doing, and who are you with?”