Chapter 4
The Art of Flirtation: From Eye Contact to Connection
Flirting should be fun, not anxiety-inducing. The stakes are incredibly low: either someone recognizes your interest or simply thinks you're friendly. Even rejected flirtation usually leaves both parties feeling flattered rather than embarrassed. Getting hit on is an ego boost, and the worst-case scenario is simply that someone doesn't reciprocate, which isn't that deep.
There are five types of flirting: immature, online, mature, relationship, and friend flirting - but the baseline for all types is respect and taking cues from the other person to ensure their comfort. Immature flirting aims at physical connection - going home with someone, making out, or starting a casual hookup. It typically happens at night in bars and clubs, requiring confidence and a short-term goal.
Eye contact is the perfect low-stakes signal of interest. Hold eye contact for three seconds, three times - it's foolproof. If they're interested, they'll likely approach you. But respect boundaries - back off if you see them with someone else, as you wouldn't want someone flirting with your partner.
Confidence is the ultimate accessory when flirting. We attract the energy we put out - to draw in a confident, fun, exciting person, you must exude that same energy yourself. Being willing to put yourself out there and caring less about rejection gives you better odds than passively waiting to be approached.
After establishing physical contact through wave one (like comparing hand sizes), move to wave two: pay them a compliment. Compliments are flirting currency because everyone likes to be complimented. For men especially, complimenting their eyes can be effective since they rarely receive such compliments.
Wave three of immature flirting involves creating an inside joke - find anything to poke fun at together. If you have nothing else to work with, ask them to take a shot with you. If you've successfully navigated the first three waves, it's time for wave four: leaning in for the kiss. Those three seconds before kissing someone in a bar are electric - the world blurs around you, creating one of the most romantic and tantalizing human experiences.
You can tell what someone wants based on how they flirt with you. If someone is immature flirting, they're likely looking for something casual or fleeting. Accept this reality rather than trying to change their intentions. You deserve someone who actively wants to be with you, not someone you have to convince.
Flirting isn't just for starting relationships-it's essential for maintaining them too. Even in established relationships, flirting keeps the connection alive and vibrant. Just because you've been together for years doesn't mean you should stop saying "you look hot tonight" or being playful. Be intentional with compliments, physical touch, and playfulness. Comfort can breed complacency, so make the effort to keep flirting with your partner, whether you've been together five months or five years.
Chapter 5
First Date Fundamentals: Creating Connection Without Pressure
First dates should be approached as low-stakes encounters that result in either "a good story or a second date." After approximately fifty first dates in New York, I learned to evaluate whether I liked my date rather than obsessing over their impression of me. This shift in perspective was transformative - instead of placing the other person on a pedestal, as though I was waiting to see if I'd made it to the next round, I could view us on equal footing.
Always prioritize safety on first dates by setting up a check-in system with someone you trust. My mother asks for a thumbs-up emoji from the bathroom to confirm I'm safe without interrupting the date. Establish a similar system with friends or roommates because unfortunately, stranger danger is still real.
Create a pre-date ritual to manage anxiety, as the anticipation of anything is more troubling than it actually occurring. Having a consistent routine provides stability and control when facing the uncertainty of meeting someone new. My ritual involves wine and Ariana Grande music, but any comforting routine that takes the edge off works.
Wear an outfit that makes you feel confident rather than trying to appeal to your date. I alternate between my "Canadian tuxedo" (denim on denim) and "Eff Me sweater" - both representing confidence and self-respect. My Canadian tuxedo became my "confidence uniform" after posting a photo in it that made an ex regret his actions, reminding me to never accept less than I deserved.
Be yourself on first dates but provide an "Eli-lite" version - authentic but slightly reserved. Don't reveal everything immediately; share one comedic trauma story to create connection while saving deeper revelations for later dates. I experienced a different kind of euphoria being sexy to someone when I was being myself - ordering what I wanted, speaking confidently about my theater degree, and setting clear boundaries about not sleeping with someone on the first date.
Having a go-to drink order builds confidence on dates. I recommend beverage-centered first dates (coffee or drinks) because they give you something to do with your hands and facilitate conversation better than activity-based dates. When meals are unavoidable, I recommend restaurants where sharing plates is normal.
Ordering nachos on a first date reveals character. I believe watching how someone shares nachos predicts their generosity in bed: "If a person leaves all the best nachos with all the best toppings on your side of the plate...they're going to go down on you without you having to ask. If they're a selfish nacho eater, they're selfish in bed."
Make a decision about wanting a second date before leaving the first one to avoid the anxious post-date waiting period. Be direct with phrases like "I had a lot of fun tonight...LMK if you want to do it again sometime!" Text first if you're interested - it won't change someone's mind about you. They already know how they feel, as do you.
If you're not interested after a first date and they text you, send a polite rejection message rather than ghosting, which is disrespectful and immature. Be honest (don't offer friendship if you don't mean it) and remember that nobody is ever too damn busy to send a text.
First dates have helped me learn about myself - my preferences, boundaries, and desires. They can be the beginning of building an emotional home with someone if it works out. Even if most first dates don't lead to relationships, you'll always walk away with something valuable, whether it's a story, a second date, or simply the motivation to try again.
Chapter 6
Beyond Chemistry: Building Meaningful Relationships
Second dates are more complicated than first dates because there's more emotional investment. While chemistry is essential, it's only 20% of what makes a successful relationship, and it's impossible to know on a second date whether you'll have long-term compatibility.
I once had a rain-soaked second date at Chelsea Market with a man named Nate, where intense chemistry led me to mistakenly believe we were destined for a serious relationship. Though we had strong attraction and connection, I learned that chemistry alone isn't enough to sustain a partnership. On a second date, you can determine if there's chemistry, but not true compatibility.
Choose yourself first. Like yourself and enjoy your own company. Not everyone will like you, and that's okay - it's not a reflection on your worth. I used to fall for the idea of someone rather than the actual person, creating a fantasy version of my date in my mind and imagining a future together before truly knowing them. This led to disappointment when they turned out to be regular humans rather than the idealized partners I'd constructed.
For those dating with intention, the second date should happen within 7-10 days of the first date. Do something different from your first date - if you had coffee, go to dinner; if you had drinks, try mini golf or a picnic. Getting to know someone in different environments and times of day gives you a more complete picture of who they truly are.
Don't save a date's phone number in your contacts until after the third date. This helps avoid premature attachment, especially for those with anxious attachment styles like me. I maintain a healthy mindset by continuing to browse dating apps before dates and making backup plans with friends.
Sometimes the best relationships build gradually rather than exploding with immediate fireworks - "a slow crescendo to the loudest point" rather than "an immediate symphony." Attraction and love can grow over time, and comfort can be more meaningful than intense butterflies.
As we progress to third, fourth, and fifth dates, it's time to make decisions about compatibility. I once dated "Hometown Boy" - a seemingly perfect match who checked all the boxes on paper but didn't ignite any genuine feelings. Despite good conversations and pleasant dates, something was missing. By the third date, I realized I needed to be honest rather than string him along.
By dates three to six, it's essential to categorize where you see the relationship going. Look for signs like purposefully meeting their roommates or friends, developing inside jokes that carry forward to later dates, making future plans together, and diversifying your date activities beyond the standard drinks and dinner.
By the third date, it's time to show more of your authentic self rather than maintaining a perfect "first date personality." While you shouldn't unpack all your childhood trauma yet, you shouldn't hold back so much either. I wanted my date Noah to see my more casual, everyday self with less makeup and comfortable clothes - someone who "talks too much," is "a little too loud," and "tends to be pretty messy." I believe in authenticity, not wanting someone to fall in love with a false version of myself.
Chapter 7
Navigating Heartbreak: The Path to Healing
May in Ann Arbor is the best version of May I've ever lived - 45 degrees in the morning, 71 in the afternoon. That first May, I was packing up my dorm room when Ezra came over. We hadn't seen each other since March, after a night where he'd invited me over only to force me to enter through the fire escape, sleep with him, and kick me out afterward. "Get the fuck out," he kept saying, as though he hadn't been the one who invited me there.
People ask why I went back. I think we need to stop asking those who were manipulated why they had no self-respect, and start questioning what manipulators do to make someone feel so worthless. In toxic relationships, you often can't see clearly what's happening - I couldn't just stop loving him, even when he hurt me.
"You're going to kill me," Sadie said. "But the only thing that really helps is time." I nodded but secretly told myself I'd prove her wrong. I thought beautiful, audacious girls like her had it easier, so their advice had to be false. But she was wiser, and I, drenched in naivete, was determined to find another way.
The truth is, you have to greet your pain, meet the hard feelings halfway, get to know them in order to say, "I've had enough of you, you can go now." You have to hold something before you can let it go. Give yourself days, weeks, or at least a weekend of watching romantic comedies, eating ice cream, and feeling sorry for yourself. It's an integral step in healing. Then set a date for the wallowing to end - shower, clean your space, take a walk, and put one foot in front of the other.
Remember there's no timeline. No "supposed tos." No one correct way to handle heartbreak. It's allowed to feel awful and strangely freeing. It's allowed to be devastating even if you initiated the breakup. Do something for yourself - a haircut, some fresh highlights - make yourself feel refreshed in this period of newness.
Take it one step at a time. Don't start dating until you're ready. Maybe first try a dance floor makeout, then a first date with a stranger, eventually sleeping with someone new when it feels right. The heart is a muscle - when you pull a muscle, the doctor says take time off, don't do anything that hurts, stop and rest when it does. It's the same with your emotional heart.
We cannot convince someone to want to be with us. And we shouldn't beg to be someone's maybe when there's someone else out there waiting to look at us and say "fuck yes." We shouldn't have to beg someone to be with us. Go where you are wanted. It's the key to not crawling backward into the arms of an ex who will never want you the way you want them to.
Sometimes the best days of your life aren't about romance at all. They're about running miles in the blaring heat, reading on a park bench alone, standing backstage as live theater rushes through your blood, eating tacos in your apartment. The person you thought you needed might not fit into those days. Loving someone isn't always enough.
Eventually time passes, and you slip into a version of yourself you really like. What you miss isn't the person - it's the feeling of loving them, a feeling you'll have again. What you're grieving is a feeling that came from within you, and you have the power to feel it again. Heartbreak is beautiful - love cannot exist without it, like plants cannot grow without water. Accepting heartbreak as the other half of love's equation softens the unavoidable blow.
Chapter 8
The Power of Friendship: Our True Soulmates
Our friends are our soulmates - the people we often take for granted while worrying about romantic relationships. After receiving news of her mother's best friend's sudden passing, I realized the profound depth of friendship bonds. My mother and aunt had been inseparable since childhood, planning to retire together in matching rocking chairs. This loss made me reflect on my own friendships, particularly with Sadie and Daphne, and recognize that there's no relationship more concrete than friendship.
My friendship with Daphne continued despite long distance when she moved to London. Daphne - brilliant, knowledgeable about everything from pop culture to mathematics - has been my biggest cheerleader, attending my first play production and supporting me through relationship struggles. During a vulnerable moment discussing a potential reconciliation with an ex, Daphne demonstrated true friendship by pledging allegiance to me regardless of my choices. "It's you and me," Daphne would say, proving that friendship love can be abundant and more than enough.
Date your friends intentionally. My friendship with Sadie mimics a romantic relationship's honeymoon phase - we haven't gone 24 hours without speaking since we met. While we plan special outings with romantic partners, we often neglect this with friends. Friendships deserve date nights too - one-on-one dinners, cooking together, movie marathons, wine nights, walks, workout classes followed by coffee. These activities keep friendships alive, stimulate early connections, and reinforce long-term bonds.
Create consistent friend rituals. My friends organize biweekly dinner and game nights, rotating between apartments. We bring homemade desserts, wine, dietary-specific dishes, flowers, and cheese. Between these Thursday gatherings, we maintain individual connections through one-on-one outings. Nobody feels threatened by these separate friendships - instead, they strengthen the group as a whole. Like romantic relationships, communication and trust allow us to celebrate each other's individual friendships rather than feeling jealous.
Build community to survive your twenties. Especially in big cities, the community you create functions like a trust fall or home-cooked meal - providing comfort and reassurance. Having a chosen family (even if you have a wonderful biological family) is essential for thriving in your twenties.
Show up authentically in friendships. My friendship with Jen from graduate school taught me to be myself when meeting new people. Before Jen, I would wear a mask or facade, trying to be who I thought others would like. Now I show up with my "heart stitched right on my sweater sleeve," knowing that true friends will want me as I truly am, not some manufactured version.
Three-person friendships can work with trust and transparency. Despite the common belief that three-person friend groups inevitably leave someone out, they can thrive with open communication. Each pair within the trio may have their own inside jokes and bonding points, but when all three come together, there's no drama or negative energy.
Treat friendships like romantic relationships. Friendships aren't much different from romantic partnerships - they require work to build and maintain. Sometimes we experience friendship heartbreak, grow apart, or reconnect later. We might surprise ourselves with new friends who are different from us but somehow work well together.
Quality matters more than quantity in friendships. At points in college when I had only one friend, that was enough because that friend was worth more than "ten shitty friends combined." The number of friends doesn't dictate personal worth. Despite past social anxiety and fear of rejection, I've learned to believe in my value as a friend and person. I cherish friendships even when they're few in number or limited to monthly coffee dates.
Chapter 9
Honoring Your Life: Authenticity Over Romanticization
My first word was "wow" and my name Eli - traditionally masculine - which I initially disliked but grew to appreciate for making me memorable. The concept of "honoring your life" is an alternative to romanticization, which creates false expectations and disappointment. Instead of idealizing life like a movie script with a perfect ending, embrace reality while finding ways to elevate it within your current means.
Avoid setting rigid end goals that limit your potential. While making goal lists is valuable (I love manifestation), remember there's always something more to achieve. Keep your aspirations open-ended so you can surprise yourself with what you might accomplish beyond your initial expectations.
Take gradual steps toward improvement rather than expecting immediate transformation. Honoring your life means creating routines that ensure enjoyment and memory-making within realistic parameters. Don't wait for external salvation - like meeting Prince Charming - but instead do the internal work needed to "save yourself." Focus on making your current reality beautiful and fulfilling through achievable, tangible actions.
Make choices you authentically want to make, not what you think others expect of you. When faced with decisions like choosing between studying abroad or taking an internship, ask yourself what YOU truly want. Becoming the CEO of your own life means taking control of your decisions and recognizing that no one else can genuinely tell you what's right for your own happiness.
Simplify decision-making by putting facts before feelings. Lay out all the information first, then decide how you feel about it. Recognize that you are in control, and you can mute the external noise to make clear-headed choices that align with your true desires.
Start with low-stakes choices to practice making decisions for yourself. Begin with simple things like how you want to dress, what you want to eat, where you want to go. Ask yourself the questions you'd ask others seeking advice: How does that make you feel? What do YOU want to do - not what you think you should do?
Show up in life authentically as yourself, even if it means losing people who only liked a curated version of you. Embrace your true style, preferences, and personality. You'll lose inhibitions, phony friends, and superficial attention, but you'll gain self-respect and attract people who appreciate the real you. When you honor your authentic self, everything eventually grows brighter.
Allow yourself complete honesty in your private moments. Journaling can be a powerful tool for facing truths you might otherwise avoid. Time moves relentlessly forward, but capturing your raw thoughts helps you process experiences and recognize patterns in your life. Let yourself be vulnerable with yourself first.
Recognize that confidence is the foundation of feeling good in your own skin. Years that challenge us often teach us the most valuable lessons about ourselves. True attractiveness comes from self-assurance and liking yourself - when you embrace this energy, it shows.
Write down a realistic but ambitious vision of your ideal life, then identify what needs to change to achieve it. Often, the most profound change needed isn't in external circumstances but in how you view yourself. The ideal life might simply be one where you're content, free from self-criticism, and doing whatever makes you happy. You only have control over how you feel about yourself - and that's a perfect place to start.
