First dates: stop playing it safe

Want more first dates? Stop playing it safe

Want more first dates? Maybe you need to stop playing it safe. If dating feels like a rollercoaster, chances are you’re ready to get off. You’re ready to cancel all the guys who say –let’s do this again sometime, but never follow up. If you want more second dates here’s what you need to try instead.

When it comes to your self-esteem one minute you’re up, the next you’re down. Dating can be ambiguous, you don’t 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 too 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.

There’s now more competition

There are more single people than ever in the dating pool. The last ten years have proven to be difficult for people who are online daters. 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

Playing it safe: 
  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 unlike 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 the 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 prep 

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 me 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 it you both 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 and interested

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 or tell a good story they might look at you cross-eyed. Often what makes you interesting is your philosophy on life, or 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. Ask good questions and show that you are interested back.

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. People connect talking about these same topics because they are more emotional. Without sharing enough about yourself you run the risk of being vanilla. 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.

Don’t be afraid to flirt

First dates are supposed to be flirty, that’s why they are fun!  How else can you let a person know you interested in being more than friends? First dates should have a bit of sexual energy. A way to express interest is through touch. Don’t give someone the creeps by being too handsy, and make sure that the feelings appear mutual. You certainly don’t want to offend someone or make them uncomfortable. A gentle touch on someone’s arm or leg is 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 your date 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. Why leave fate to chance.  You can show interest on the spot and plan your next adventure.

Maybe say, ‘That art exhibit you mentioned sounded awesome, I’d love it if we went together next week, what do you think?’ If the interest is mutual they will be relieved they have you down in their schedule.


The best thing you can do on the first date is to Lighten Up! Why take dates so seriously? 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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Sending you so much love,




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