6 Dating Tips for Introverts

Even in the best of circumstances, dating can be difficult. But if you’re an introvert, it can be all the more challenging.

Sometimes it feels like dating is all about extroverts, or pretending to be an extrovert. Friends, family, and co-workers tell you to “Walk into a room like you own it” or “Go out to a different place every night” or “Talk to 20 people a day.” It can feel like all the attention, press, and spotlight goes to those outgoing individuals.

The introverts of the world tend to have a few more hurdles to overcome in the dating arena — and that’s OK.

Just because there are a few more, or perhaps just different, challenges, doesn’t mean love is going to pass you by in any way. I’m married to a self-described introvert. And, as many of you know, being an introvert does not mean being a hermit. It just means introverts recharge their energy by spending time alone.

For all of you introverts out there, here are some dating tips to help get you happy and excited about dating again.

People have a general dislike for small talk. It can feel fake and forced. And, if you’re an introvert, it can be painful.. But, if you want to meet someone new, a little preliminary chitchat to get the ball rolling is necessary.

We can’t just jump right into deep discussions. Conversations are one of the first ways we find out if a person we have just met shares something in common with us, and for us to demonstrate our compatibility with them. To build relationships or deep friendship, we need to go through four levels of intimacy:

• Social
• Connection
• Comfort
• Intimacy

As tempting as it may be to jump straight into Netflix and sweats, we need to move through these four levels of intimacy.

Social intimacy is when you just met someone and are starting to learn about them. You are asking getting-to-know-you questions (i.e. “Where are you from?” “What do you do?” “Where did you go to school?”).

I equate this to fishing. You are throwing out a bunch of different lures to see which one gets the most action on it.

Whatever questions your date responds well to are the things she values, so you can start to hone in on likes. Once you find something you both like or value, you can move to the connection intimacy level and can continue through the progression.

As I said, dating can be nerve-wracking for the best of us, so you don’t have to pretend that it isn’t. But think of this as an opportunity to turn a weakness into a strength.

If you are trying too hard to put up a confident façade or trying to portray a person you aren’t, it’s going to make you even more anxious and could backfire. Instead, just admit what we all know: This whole dating thing is kinda silly and weird. You can say, “I’m sorry. I’m a little nervous right now. I don’t get out as much as I should, so sorry if I come across as a bit shy.”

In “The Art of War,” which was written sometime around the 5th century B.C., the author, a Chinese general and philosopher, lays out tactics and plans for battle. One lesson is to turn your weaknesses into strengths.

I coached a guy who had a big facial mole that he was very self-conscious about. After working with me, he’d go up to girls and ask, “Hey, my mole and I would like to buy you a drink.” They would laugh because he had diffused his own anxious bomb and showed he was OK poking fun at himself.

Own your introvertedness! Say something like, “Thanks for meeting me out tonight. Usually this is when I put on my formal sweatpants and watch ‘The Office’ for the 16th time.”

One of the biggest missteps I see with my male clients is watching them have a fun interaction with someone, and then they flog it to death until it runs out of energy.

Life is pain vs. pleasure, and we’re trained to leave pain and move toward pleasure, but sometimes we need to flip this script. Sometimes we need to move toward pain (i.e. working out) and move away from pleasure (i.e. a second donut).

Coffee dates are great for a first meeting because there’s kind of a deadline, so you don’t have to feel pressured to stay if you don’t want to.

You want to leave while the energy is still high. Leave them wanting more, and leave them with a good taste in their mouth.

I know the coffee date is much maligned, but don’t put yourself in a situation where you’re going to accidentally sabotage yourself. Go for a quick walk in the park or to a holiday fair. You can even plan it before something else you have to do, so you can give yourself a hard end. Just say, “I have to pick up something downtown at 2, so I wanted to see if you wanted to meet up beforehand at 1.”

As we know, there are different levels of being an introvert. Some introverts really don’t like loud and busy places, while some are OK with that but in small doses.

If you’re someone who is anxious around crowds, don’t make a date at a packed restaurant. You want to go somewhere with the least number of distractions for you and your guest.

Go somewhere or do something that you know or can talk about. This gives you something to discuss as well as a way to demonstrate value. If you’re a writer, have a date in a bookstore. If you know about gardening, go to a botanical garden.

Yes, each date is different, but dates, in general, tend to follow a lot of the same templates. For instance, your date is going to ask you questions. What kind? Probably the first few normal ones like, “What do you do for work?” “Are you close with your family?” and “What are your interests?” How are you going to answer?

I find it interesting that in our jobs, we are very conscious of preparing for outcomes to maximize our benefit, but we don’t seem to do the same thing in our personal or dating lives. If you know your date is going to ask these questions, prepare a few answers. That way, you won’t be fumbling for what to say when she does ask you.

When I was single, I used to check out weird news sites before I went on a date so I could come into it with at least one interesting thing to bring to the table. For example, “Did you see ‘My Octopus Teacher’ yet? It’s about a guy who befriends an octopus and learns a lot of lessons from her. Oh, it’s not animated. It’s a documentary.” Give it a try and see if it works for you.

I know that for a lot of my dating coaching clients, the end of a conversation or date can be the most anxiety-inducing. So I recommend planning an exit strategy.

For the end of a conversation, you can say something along the lines of, “Well it’s been great talking to you. I’ve got to go now. Be well.”

When it comes to the end of a date, it could go lots of ways. Everything from the awkward hug to swinging from the chandelier. But you can plan out a couple of ways you could play it, depending on the circumstances.

Come up with a few different scenarios for how to end the date and what you want to say. That way you’re not dreading your date and always looking at your watch to see when it’s time to go home.

If it’s going well, you can suggest that you meet up the following week at the thing for the event. If you’re not sure, you can talk about how you are having fun and hope they are too, and judge their reaction. If you’re not sure whether to go in for the kiss, maybe give her a hug and kiss on the cheek and see if it develops into something.

None of it will go exactly how you plan it, but at least you’re ready for a few possibilities.

I know we’re all going through a pretty rough right now, and while some people make jokes that this is the perfect time for introverts, studies show that the pandemic is actually proving more difficult for introverts.

Just because you’re an introvert and can’t go to work or anywhere else right now, that doesn’t mean you should completely remove yourself from society.

In fact, it’s a great time to try some new things right from the comfort of your own home. Engage online, take a virtual class, try improv lessons, start a blog. These can all be outlets to new relationships!