How to Make Your Introverted Date Feel Comfortable
Introverts can be excellent conversationalists who are a lot of fun to date — but first we have to feel comfortable with you.
We introverts are curious creatures. Many people think we’re recluses whose voice boxes have rusted over from lack of use, and what’s more, the truly misinformed think that’s the way we like it. So not true. Introverts can be excellent conversationalists who are a lot of fun.
There’s just one thing: We have to be comfortable with you first.
We despise the getting to know you part of dating because we hate the superficial, “How was your day?” or “The weather’s been great recently, hasn’t it?” This is where we try to play our part and sputter out a “fine” or “yes” in hidden frustration as we wait for the next painfully shallow question.
And hey, it’s okay. We understand you’re trying to get the ball rolling. But we’re in agony. Agony with a capital “A.”
Most introverts find it extremely uncomfortable to sit there and play dating games such as this one when we could be nestled in our pajamas reading our favorite poet or philosopher. And again, it’s not your fault. There has to be a starting point, and we know this. After all, it’s not like you can go into a first date being comfortable. Is there anyone, introvert or not, who can manage this? If so, tell me your secrets.
But if you find you are under the alluring spell of an introvert and want to unravel his or her mysterious nature that you find so seductive, I can help you do so by telling you how to make a really great first date.
Understand the Odds: They’re in Your Favor
There is one thing you need to understand. If you ask an introvert on a date and he or she actually says “yes” without calling to say he or she has a sudden fever or a vague “something” that came up at the last minute, then know this. He or she is interested. Probably very interested. Because we don’t put ourselves through the hell of first dates unless we sincerely want to make a connection.
So the fates are on your side. Now you’ve just got to seize the moment and make it magical.
What rabbit can you pull out of your hat to draw your introvert date out of his or her shell? Let me tell you.
Give Us Options
When you plan a first date, give introverts options. Don’t, whatever you do, plan a quiet intimate setting at a restaurant as a first date. That can be wonderfully seductive later, but not on the first date. Again, it’s that damned pressure to fill the silence with small talk.
You must also give us “outs.” Everywhere. Give us choices. An “either/or” scenario so we can better prepare ourselves. We like to plan things. At least at first.
If the situation allows during this crazy pandemic, offer to take us somewhere there are things that spark conversation. For example, an art museum, play, or movie where we can discuss what we see. Many introverts are really into the arts and like to ponder the bigger truths and ideas behind an artist’s creation. A comedy club may be another great option because we can just listen and laugh and not feel pressured to talk. Just be sure to make the club a small one where we are not overstimulated by a lot of people and ambient noise.
You also know what a lot of us like? Trivia. We are usually well-read because we live in a world of thoughts and ideas, and we love to test our brain power against you or others. It’s not a power play, it’s just fun. Some restaurants even give customers a trivia console and allow them to play against other diners.
Two more options that provide the same type of comfort and mental stimulation that we love? Mystery dinner theaters or even escape rooms.
Activities like these provide fewer opportunities for those pregnant pauses where our first impulse is to text our friend with the “safe word.” And let me tell you, every introvert has that friend who is on alert to provide us with an easy escape plan.
For example, if an introvert feels pressured, a frowny face text emoji to his or her friend may be the signal for him or her to call with feigned emotion and say, “I’ve got an emotional crisis and I need you to come now.” In this way, we can avoid hurting your feelings (we’re usually very sensitive people) and manage to escape an uncomfortable situation.
And speaking of escape plans, make us feel better by offering one yourself.
Allow Us an Escape Plan
Ask us whether we would prefer to drive together or drive separately. This also gives us an “out.” We are comforted by the fact that when our “people quotient” is full to the brim or the pressure to perform as a good date is too much, we can leave on our own timelines.
Don’t assume just because we leave early that we don’t like you; it’s just there’s only so much outside stimulation an introvert can take.
Another escape route that we find comforting? A time limit. Lie to us if you must. Tell us that you have to be at __ at __o’clock to do __. This puts a limited time frame on the date so we can “hold it together” for a little while longer if we begin to feel uncomfortable.
And I have to keep saying this because I know it sounds like we introverts are a bucket of cold water. Remember if we’re on this date, we’re interested, and time spent with you is wonderful, but our people batteries have a short shelf life and need to be recharged frequently.
Ask Us Questions
Many introverts are extremely curious people, and to fill the silence, we will try to find out more about you. But we secretly love it when you stop and ask about us. And ask us fun, provocative questions, not mundane ones. Ask us which fictional character we would most like as a friend or give us ethical dilemmas to discuss. We love the deep stuff. And if you love the deep stuff too, well, we’ll likely be drawn even closer into your spell.
Put Away the Phone
Introverts may be quiet, but we are usually very observant. We often have an intense desire to study human behavior and understand the human psyche. So when you choose to accept calls or scroll or text mindlessly, we may feel wounded. We tell ourselves we must be doing something wrong or you would be more interested in looking at us than Instagram or Twitter.
Many introverts are also highly sensitive people (HSPs) who feel things intensely, so while this kind of behavior may be off-putting to anyone, introvert or not, it may hit us even harder. After a while, into our shells we go.
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Use Humor
A bit of laughter always breaks the ice for every date. But I’ll be honest. If you are brave enough to let the humor be a bit at your expense, it will pay off in a huge way on your date with an introvert.
Why should you let us laugh at your quirks, mistakes, and failings?
Because most introverts are a bit awkward at first, and we know others see this in our behavior. So if you let us be privy to some awkward moments in your own life, it makes us less focused on our own inability to be the “social butterfly” who fits society’s stereotype of a perfect date.
The Bottom Line About Dating an Introvert
When in doubt, ask. Introverts may not be the most vocal about their needs and feelings, but when you invite us to share them, you may be surprised by how we open up. Check in with your introvert before the date about your plans to make sure he or she feels good about them — and don’t stop checking in throughout the date. That kind of special consideration will go a long way toward winning our hearts.
It takes a special person to unlock the gates to an introvert’s heart. But if you’re patient and accommodating to our needs, you may find quite a nice surprise behind our quiet exterior. We are thinkers and feelers, passionate and sensual, and once you allow us the time and space we need, we will unveil our special gifts. We may become that partner who you never want to let go. 
A version of this article was originally published on P.S. I Love You.
