Dear boy who showed up drunk on our very first date.
After you moved our meeting time three times because you were running late. You showed up fifteen minutes past when you said you’d be there, and I watched you stumble in. You looked remarkably like someone I already knew, but I tried not to notice your slight case of alcoholism. I smiled and answered your questions, as awkward and intrusive as they were. I attempted not to judge you when you finished three beers before I finished my first glass of wine and after I declined a second one, I politely waited for you to finish your fourth Bud Light. Though you did insist on paying, you also tried to insist on me coming home with you, though I had to open the cab door for you because you couldn’t open it yourself. I laughed as you asked for my number (when you already had it) and then again when you mentioned how much fun we would have if I would stay the night with you (after I already refused before). When you texted me the next day making a joke about drinking too much, I sweetly let you down, and you responded saying I should be more forgiving and go with the flow.
Dear boy who ignored me when I wouldn’t sleep with you on our third date.
I really did like you. I really did feel such a great, amazing connection with you. It was nice to have an educated, interesting conversation with someone that wasn’t based on the basics of New York: where you’re from, what you do, what part of the city you live in, OMG this weather is awful/awesome. I loved the places you picked for our dates and even more so, how you insisted on walking me home and like a gentleman, kissing me goodnight without pressuring to come upstairs. I liked how you sent me funny memes and remembered things about our conversation that I didn’t even recall, and how you set up another date before the date we were on was over. I thought that maybe you and I would be something, something more than a handful of dates or a drunken encounter – but then you disappeared when I wouldn’t give it up on our last date. A day passed. A week. And I realized that even though you talked about many wonderful things that could possibly be, the thing you wanted more than anything was to get jerked off. Sorry I’m not sorry that I disappointed you.
Dear boy who refused to leave Brooklyn on a Saturday night when the L train was down.
The first time we were supposed to meet up, you got too tipsy with friends you haven’t “seen in a long time” and couldn’t stumble your way to a bar to meet me. It was really considerate of you to cancel less than hour before our date, after I showered, walked the dog and was just about to get on the train. I did actually appreciate your sincere and honest apology, and I thought our first date was intriguing and had easy, casual energy. Your motivation and passion for what you do was inspiring and well, I loved that you were 6’3” and held doors open for me. Your follow-up text message that night and the following day were enticing enough for me to agree to a second date. And though I was hesitant about going to your neighborhood, I agreed anyway. But when the trains stopped working and I asked for a compromise that was equally convenient (or inconvenient) for both of us, and you couldn’t be bothered to move from your street (and let’s be honest, your bed, I’m guessing), I couldn’t be bothered to deal with you.
Dear boy who doesn’t know how tall he is or what he does for a living.
Your text messages were alluring and convincing – I really thought our date would be fascinating. But before I even walked in the door, I knew I had been tricked. I’m sorry, but 6’0” and 5’7” are not the same thing – not even close. Especially when I wear heels to impress you on our first date. And while I still would have gone out with you if you said you were merely interning somewhere, I was annoyed that you claimed you lived and worked here. When in reality, you’re just here for the summer. I would have let all of that slide except that you couldn’t keep eye contact for even a second in the 45-minutes we drug out that one drink. Your eyes met my breasts and my legs, my ass and my knees, but never once did you look at me. I tried to brush it off, but I probably showed my anger when as we went to part ways, you joked: “So next time, let’s just do your place.” Let’s not.
Dear boy who showed up wanting to get laid when I was running 100-degree fever.
I liked the outdoor space where we had a few too many cocktails and then went to your friend’s 30th birthday party. I thought it was odd you wanted to bring me along, but we had so much fun dancing and chatting with everyone you knew that I couldn’t wait to go on another date with you. It was so nice of you to show up not only on time, but early, and to order my favorite glass of wine so it was waiting for me. Though I couldn’t decide how attracted I was to you, I was attracted to your personality and the way you expressed yourself. I told myself not to be so picky, to give you a chance, and so I did, on another date. But then I got sick. And I was going out of town. And though I didn’t want to cancel on you, I could hardly get out of bed and barely breathe through my nose, so I did. You surprised me when you said you’d bring soup and drive me to the airport the next morning. When you showed up sans-chicken noodle and pushed me onto my bed, attempting to rip my clothes off and I stopped you, I was appalled when you said: “What, you don’t want to? It’s our fourth date.” After I sweetly kicked you out and cursed you, I made a mental note to always go with my gut.
Dear boy that I loved for three years too long.
You were the best and the worst of them all. You were a boy before we dated and I dreamed you into a man, nursed you into a gentleman and you turned right back into a boy, fooling me every move, every month, every fuck along the way. Your love and what I hoped for us was felt like a shadow extending over everything that I did – always lurking, always promising something that would never be. It took every ounce of dignity, every last slice of pride, every piece of courage I had to finally walk away from you. To block your number and send your emails to trash. To push you out of my life, my thoughts, my lingering belief in impossible possibilities. I loved you in ways that I didn’t know I could love, and you changed me in powerfully painful ways I didn’t know someone could ever inflict. And though everyone told me that it would happen one uneventful day and I never believed them, my attachment to you released in an instant. The heartstrings let loose, my tears ran dry and though you’ll always be somewhere in my thoughts, you’ll never be anything more than a memory. A bittersweet memory that prepared me for the worst of it in New York. If I can survive you, I can survive anything.
You don’t always think you’re doing it right, and more often than not, you’re embarrassed by your insecurities. You blame yourself for everything that goes wrong with some boy, some relationship, some date, even though it’s not (always) your fault. You constantly obsess about being too much or too little, if you’re pretty enough or far too picky to find that love you look for. You keep going when the going gets tough, and though you have your tantrums, you never lose hope. You never give up. And I’m proud of you for that. For never settling, for standing up for yourself, even when it’s the hardest thing to do. Even when your friends think you’re too harsh and when they give advice you don’t take. I’m inspired by how you lead your life with love, even if the love you want the most is not at reach. I know you don’t want to date yet another boy, but do it anyway. Learn from it. Write about it. Help other women. Let all of those dear boys pass through your life because they’re just making you stronger, getting you one step closer to the you that you’re meant to be.
And if you keep believing, closer to the man – not the boy – that’s meant to be, too.
PS: If you have a “Dear Boy” letter you’d like to share, comment below or email me: firstname.lastname@example.org. I’ll publish them anonymously or linking back to your blog or social account.