You Should Date More. (A Few Of) Avery’s Rules for Dating

by Avery Lender

Dating is hard (pause for shock and awe at this revelation). Our feeds are flooded with info about loneliness, Gen Z dating failure, and people 40+ who have never had a significant other. With all this, I think it’s time for me to finally step up and help.

A humble disclaimer: I have been out of the field for a while (#taken), but that never stops me from giving my advice to those in need. So here I have provided a few tips and tricks for the single and hopeful. 

Footage from Avery’s own double date. Proof of success, if you will.

The 3rd Date Rule

A first date, ESPECIALLY when it is someone you met off the apps, really is the introduction. If it was a job interview, you would ask questions about their previous work experience, their biggest weakness, to sell you this pen, etc. When we meet a new person, we have a list of questions we want to know about them. Those normally being their siblings, their job, and their hometown. I don’t think getting a little worldbuilding on a date is wrong, but it’s going to feel more like an interview than testing real chemistry, which is where I introduce the 3rd Date Rule. 

By the 3rd date, you start to feel comfortable with someone. You might already know some of these facts about their backstory and start to instead chat about more recent events. When you go into a date, don’t ask them their favorite color, but instead, what they’ve been up to that day/week. Chat about other couples at the bar or something funny you saw on the train en route to said date. I promise you that if this date goes well, there will be plenty of time to continue learning about each other on the second and (real) third date. If it goes poorly, you won’t feel like you gave a stranger your life story.

Don’t Look to IG Couples

Here’s a hot take: the only couples we should be following are our friends and A-list celebrities. I know that some of you might say that following celebrity couples is a bit lame and parasocial, but it’s been happening since the beginning of dating itself! (Antony and Cleopatra: scandal city). It is natural to be invested in the love lives of others. However, I think a big problem comes from following influencer couples. When we see celebrity couples and follow their lives, there is a knowledge that their lives will never look like ours. I live in a world where celebrities are NOT like us, and that is for the best. 

Influencers, however, make all of their money off of being ‘relatable.’ They take videos of their boyfriends bringing them daily flowers and planning extremely elaborate weeknight dates. But if you can break the 4th wall here, they are clearly doing these things to make money and get engagement from women. They can sell the fantasy of lavish surprises, but oftentimes we forget a camera has been set up for the entire thing. The more influencers make it seem that it’s all from the heart, the better their content is. This is why when these couples break up, everyone is so shocked since they had the ‘perfect’ relationship. Single people watching these videos might think that this is what an ideal relationship should be, but personally I would not want my boyfriend setting up a tripod before ‘surprising’ me with a bouquet. So, if you do need couples content, look at the least relatable instead. 

Rejection Therapy

The advice that no one wants to hear is you need to break a few eggs to make an omelette. I think we got so used to dating apps over the past 5 years or so that the concept of meeting someone ‘the old-fashioned way’ is seen as an unattainable goal. Yes, of course, many people meet on dating apps and are successful, but there is still a glimmer around those who meet IRL when they tell their story. These people who somehow broke from the E-World to make a human connection, which I am lucky enough to call myself one of. I know that talking to people is scary, but there are ways to practice!

Practice getting rejected for the little things. Go to an ice cream place and ask for a sample, and then leave without buying a scoop. If you can do that, you’re ready to give a compliment to a stranger. I know that women are more likely to compliment other women, especially strangers, so if this is too scary for you as a man, try just complimenting your friend unprompted.

Then, when you're out in the wild and see someone you want to talk to who is cute, you can start with just commenting on something in the space and see how they react. 

Examples:

AT A CONCERT: (Band) is so good live; have you seen them before? 

AT A BAR: Where do you think they got this? (about random bar decor) 

AT A PARTY: How do you know (host name)?

AT A COFFEE SHOP: I hate to say this, but in the Drama when Robert Pattinson said to Zendaya, “Oh I love that book,” I thought it was a good line; just don’t lie about it if you actually haven’t read it. 

You might roll your eyes at these examples, but I think they can sometimes be better than a compliment or buying a drink. And this goes for every gender. I still think in the big year 2026 there is a lot of stigma around women approaching, which to that I would say: it’s time to lock in. If you do approach someone, you can normally tell if they are open or closed to continuing a conversation. If they are closed, don’t take it personally, which is the hardest part. Some people might actually have a boyfriend, or just not feel your vibe, and that’s ok. My grandma says, “Every pot has its cover,” and I think that is very true. If some rando at the bar is not your cover, you gotta move on to the next.

Cupid herself.