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first dates, what to do
Communication Skills | Dating
Stop playing it safe on first dates to get more second dates

Dating often feels like a rollercoaster ride. When it comes to your self-esteem one minute you’re up, the next you’re down. Dating can be ambiguous, you don’t always know where you stand. If you’re anxious, especially on a first date, the tendency is to play it safe. You don’t want your date to know you’re invested or too excited. Instead, you play it cool, stick to neutral topics, like the weather, and work. The problem is that in a sea of so many other singles you’re unmemorable. Both you and your date walk away thinking, yeah, nice, but no big spark. Here’s why you need to stop playing it safe and what to do instead to get more second dates.

more competition

There are more single people than ever in the dating pool. The unspoken expectation is you don’t have to settle. Every day you get new singles pushed to you by your dating apps. It’s easy to have the impression there’s an unlimited supply of singles. Meeting IRL can fall short compared to your imagination. Somehow people look more interesting on an app than they do in person. With the illusion that a better mate is one swipe away everyone keeps searching for a unicorn.

But thinking of it as a dating game won’t help either, you want to avoid the common pitfalls of first dates:

common first date fails

  1. You don’t prepare
  2. Your dates are too short or too long
  3. You’re not particularly unique or don’t show enough interest
  4. No flirting, weak finish

dating is different from other social encounters

Dating is unlike other social situations. You need social skills that are different from hanging out with your friends. When you’re hanging with your friends, you’re the life of the party, your witty and quick with a comeback. But when it comes to first dates you clam up. You don’t have a history with this stranger, you don’t know their sense of humor. As a result, you fumble for something to say, “what do you do for fun?” Sticking to safe topics is a recipe for a disaster.

lack of preparation 

Sure you take a shower to prepare, but that’s about it. While you don’t want to think of a first date as an interview, first dates and interviews are similar. If you don’t make a good first impression on a first date there certainly won’t be a second.

If you want to make a lasting first impression spend time thinking about what makes you special. Prepare a handful of stories about yourself that tell more about your personality. It’s fun to poke fun of yourself, tell about that time a squirrel fell on your head, or when you mistook your neighbor for your boyfriend. By being vulnerable and opening up you allow your date to do the same. Before you know you are connecting on a deeper level.

Leave them wanting more

Plan where and when to meet for your date. If you schedule a last-minute coffee date at Starbucks before a work meeting, don’t be surprised when she decides to take her coffee to go. Another problem is the first date that has no obvious ending. You meet on a Saturday for Brunch. Brunch turns into a walk, which turns into dinner, and then late night cuddling at his house. Your marathon date leaves you feeling like you’ve known this person forever. The issue is too much of a good thing, is exactly that too much.

The perfect first date lasts anywhere from two to three hours max. The best dates are in the evenings after work when you are not rushed or on the weekends. Two and a half hours or so is the perfect amount of time to pique someone’s interest while not overwhelming their senses. Where you meet for your date is equally important, pick someplace with ambiance. It should be comfortable and inviting, a local coffee shop or bar or restaurant.

be interesting.

If you want someone to be interested in you, you must be interesting. What does it mean to be interesting? You might be a fascinating person with lots of interests, but unless you know how to engage your date about the topic they might look at your cross-eyed. Often what makes you interesting is your philosophy on life, your goofy family or friends, your political or activist interests, your search for the perfect taco or wall art.

Are you looking for a partner who enjoys the great outdoors and wouldn’t be freaked out camping? Do you want someone to be able to go to your favorite music festival with, to travel with? Be prepared to talk about the things that matter to you most.

safe topics

Throw away your list of first dates safe topics. It’s an unspoken rule to avoid talking about politics, religion and your ex. But you connect talking about these same topics. Without sharing enough of yourself you run the risk of being vanilla. It’s not what you talk about it’s how. Be careful not to be offensive, read when things are going south. Look for what you have in common but also the things you both hate. In one article they claim that the key to a great relationship is hating the same thing.

Be interested

Think about a date similar to a game of tennis. You’ve lobed the ball over the net with your interesting topics and funny stories now you have to return the ball to keep a conversation going. How do you respond to your date?

You can acknowledge your date by saying, ‘I hear you.’ Being aware of your body language is another way to show your interest. Make sure you sit directly across from your date. This way you can look them directly in the eyes. Looking into someone’s eyes is an instant way to connect. When they are talking, make sure you smile, you’re saying, I’m listening, I hear you. Nod your head, give them approval that agrees with their sentiment.

don’t be afraid to flirt

Different than an interview first dates are supposed to be flirty. How else can you let someone know you are interviewing for a position that it more than friends? First dates should have energy that creates sexual interest that is less overt but more anticipation. Another way to express interest is through touch. Make sure that you are not giving someone the creeps if the feelings are not reciprocal. No one wants some guy to get handsy with them if the message is NO. A gentle touch on someone’s arm or leg are enough to show interest.

Successful first dates naturally are positive. Chemistry is not purely attraction but undeniable energy between two people. There is something about this person that jives with you. More people will be attracted to you once you improve your positive vibe. Some call it the law of attraction. But I call it the positivity effect!

weak close

Don’t wait till the end of your date to express interest in seeing your date again. Playing it safe is, ‘hey we ought to do this again.’ It’s a non-commitment, something similar to ‘don’t call us, we’ll call you.’ Another weak close is to presume you can ask them out on the text later. Sure you can, but why leave fate to chance. Why not start planning when you will see them again.

You say, ‘I mentioned that art exhibit you sounded interested, why don’t you go with me next week?’ If the interest is mutual they will be relieved they know when they will see you next.


The best thing you can do on a first date is Lighten Up! Why take dates so seriously? They are supposed to be fun, right?  If you want more second dates, show up prepared, be authentic and close strong. Show more of your exuberant personality that your friends and family love so much. Who knows, maybe when you risk more you actually risk far less. For daily tips, inspiration and laughs, follow me on Instagram @backtolovedoc.






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