How To Make A First Date Less Awkward
Let’s be honest, dating in this day in age is straight up STRANGE. While we may meet some romantic interests in real life (at work, at school, through mutual friends, etc.), often we’re meeting on dating apps. When it comes to actually meeting up with someone for the first time, regardless of how you came into contact, it can turn into an experience you dread rather than one you’re excited about simply because of the potential to feel so much awkwardness! Not to fear though - there are some tried and true tactics before, during, and at the end of the first date that can curb some of that awkwardness and help you re-establish a positive and healthy relationship to dating.
Setting The Stage
If you’re nervous about where you’ll be or what you’ll do on the date, be proactive and offer an idea up first. Most people will welcome the initiative! You can offer up a spot that you feel comfortable in, is close (or far) from your home, that you know has non-alcoholic options, or any other characteristics you think are important. If the thought of picking a place or activity makes you anxious, then hold back and let them take the lead a bit! You can always propose a different option if they suggest something you’re not comfortable with or that you envision may be a bit awkward as a first date spot.
Ah, the age old question: who pays on a first date? People tend to have very strong opinions about this - all of which are valid. Especially when it comes to someone who closely identifies as a man going on a date with someone who closely identifies as a woman, the part of the date at which the check comes can feel particularly awkward. When it’s a date between two people who closely identify as the same gender, or are non-binary, it gets even trickier. A good way to avoid this sticky situation if it makes you anxious is to choose an activity that is cheap or free! This is a good tactic if either 1) you’re not sure who is going to pay and you want to make sure you can afford it if you decide to split it; 2) you feel strongly about paying for your date but you want to feel comfortable with the amount you’re spending; and 3) if you feel strongly or have a preference that your date pays for you, but want to make sure you can afford it if they want to split the bill. Coffee and a walk in the park is an excellent inexpensive first date idea! You could also go to a free or inexpensive museum, have a picnic, etc. The sky’s the limit!
Take the pressure off of this date! It can feel like there is so much on the line when you go on a first date - you’ve spent time talking to them online, you have some preconceived notions about what they’ll be like, and you may have high hopes for how it will turn out. Try to remember that this is a first date - this may not end up being the love of your life and that is totally ok! All dates can have immense value, even if they don’t turn into a second date. You’re going to learn something new: either about yourself and what you like or don’t like, about a new person, or about something that comes up in conversation! Try not to approach the date with an all-or-nothing mindset. Additionally, try your best to come with an open mind. Though many of us may believe that first dates need to make sparks fly and butterflies jump, very often the people we’re most compatible with actually make us feel calmer or more comfortable than spark-y. If you like what the person had to say, their outlook on life, and/or the values that they’ve shared, it could be a super successful first date even if you didn’t feel those stereotypical sparks. This may be a person you could develop a healthy and amazing relationship with down the line!
Come Prepared
Brainstorm what you already know about your date, and what you are curious about. Come prepared with a few questions you want to ask that will help you get to know those things about them. Some examples may be:
Hmm their profile says they work in advertising, but I’m curious how they decided on that career path. → How did you get into advertising or decide that that’s what you wanted to do? Is it more a creative pursuit or a business-oriented decision?
I love that there are pictures of them with their dog! I’m curious if they’ve always been an animal person, and would they be open to being around my cat?? → Your dog is so cute! When did you get them, and did you grow up with animals? Are you purely a dog person or open to all?
They’ve seemed funny on their profile and in our texting! I’m curious about their sense of humor → Your messages made me laugh! How would you describe your sense of humor? Do you think you got that from you parents ?
Come with a few fun stock questions that you can put out there if there’s a lull in the natural getting-to-know-you conversation. These help loosen up the mood a bit, and also help you to get to know them in a different way! Some examples could be:
If a close friend was asked to describe you in three words, what would they say?
If you were going to open up a food truck of your choice, what would be the specialty item you would serve?
What has been your favorite way that you’ve spent celebrating your birthday? Why did you enjoy it so much?
Saying Goodbye
Come to the date prepared with an “out.” Especially if you’re meeting up with someone for the first time, you’re not totally sure if you’ll vibe with them at all (or, worst case scenario, if you’ll feel safe or comfortable with them). At the beginning of the date, let them know about some kind of time limit you have for the date. This could be something like “just so you know, I’m meeting up with a friend for dinner after this so I’ll have to go around ___. Just wanted to give you a heads up!” If the date ends up going really well and you want to keep hanging out, you can always say that your plans got canceled or postponed and keep on keepin’ on. But it makes it way less awkward to leave the date early or to have a more natural ending if you already told them when and why you’ll have to go!
Towards the end of the date, it might be helpful to excuse yourself to go to the restroom so you can have some time to think in preparation for the end of the date. Take a few minutes to reflect on the date so far, and how you would ideally like the date to end. A lot of people may believe that a successful first date always ends with a kiss - that is absolutely not the case! Plenty of amazing first dates can end without a kiss or any form of physical contact - and it definitely doesn’t mean the person didn’t enjoy the date or doesn’t want to see you again. This also means that you shouldn’t put any pressure on yourself to end the date with physical contact if you’re not feeling it - you can still go on a second date with them, or not, even if there’s no physical contact. This alone-restroom time is a good chance to check in with yourself: how would you like the date to end? Would you want to walk home together, or are you going to take the train/bus or a car home? Do you think you’d want a hug or a kiss, or not? What might you say at the end of the date to say goodbye? Having some of these questions answered, and a bit of a game plan can make the end-of-date jitters a little less intense. Of course, it probably won’t go exactly as you imagined, but this planning gives you more autonomy and more clarity about how you want to proceed.
If You Really Want To Skip The Awkwardness, Check Out STST Speed-Dating!
If you want to get a bunch of first dates done in one fell swoop, are sick of dating apps, and/or want to use question prompts that help you get to the core of who the person is faster, you may want to check out Skip the Small Talk’s Speed-Dating events! We currently offer them in Boston and NYC, with more cities coming soon! Check them out and grab tickets!