After a tumultuous year of terrible, no-good, horrible dating, I recently found myself not only a little bitter, but really, really disappointed. And angry. So of course, I do what helps me more than anything: writing. Though it’s not that healthy to go back down memory lane – especially one that’s jagged and misleading – but getting out frustrations (no matter how small or large) can help you move forward. For me, the “Dear Boy” letters were not only therapeutic, but freeing. As soon as I clicked publish, I released the boys back into the universe, back to wherever they came from, far, far away from my thoughts and my confidence.
When I invited all of you to submit your own – I was completely blown away by the response. It’s the thing I love most about my blog – every time I think I’m the only one feeling burnt out on dating, I read stories from around this city, this country and this planet that remind me I’m definitely not alone.
Since I received so (so!) many letters, I’ll be publishing half today and half on Monday. Each round will end with what I find the most important parts: a letter to a man worth all this trouble and a letter to the biggest love of all: yourself.
In no particular order, your amazing Dear Boy letters, part one:
Dear Boy who is exact reason why I cringe at the thought of online dating.
The moment I said..”okay, let’s give this a chance” you ruined it for me before I even realized. The moment you called to tell me you need to push back our first date for a few hours, I should have shown you the door. The moment we both finally met that night for the first time, I should have shown you the door……BUT I didn’t. The moment we kept meeting for dates (on your side of town) and you never picked me up, I should have shown you the door. The moment you kept using dental school as an excuse for everything, I should have shown you the door.
The moment we went a month without “real” communication or seeing each other, I should have shown you the door. (texting doesn’t count) Wait, I tried to show you the door but you promised you would do better & try better—and I let you back in.
I went through 6 months of “moments” with you, praying for God to grant me patience to see this “relationship” through (after all we had met each other’s parents). I also prayed for clarity from God and he gave that to me. That is why I finally showed you the door. You were my first sip of a relationship in years and if that is what a relationship is supposed to be then I don’t want it. It’s supposed to be 50/50 no 70/30.
The audacity you had to show a lack of emotion the last time I broke it off proved to me even more so that you aren’t my soulmate that God is preparing for me. I bid you final farewell and I truly hope you finally find your soulmate as I know mine will be sent to me when I’m ready. -Tiffani
Dear Boy who wanted me in secret. Who I met at work over a year ago and began to pursue me even though you weren’t my type and there was some talk of you having a girlfriend. You continued to invite me out with other co workers and then on a date which I finally caved in, merely for the excitement of where it could lead. People used to tell me so many marriages start at work. What was I thinking! I had decided in my head you were one thing and after 8 months realized you were something different. The excitement of a secret relationship at work quickly faded when you stopped reaching for my hand under the table or kissing me in the street. Sure, sex was good and the consecutive texting throughout the day led me to believe I was a constant thought on your mind. But after several months I was ready to introduce you to my friends… and even family. After catching you in several lies, and continuing to set myself up with disappointment I wised up. No more lame excuses and shame on me for being tricked by someone who was never going to commit and didn’t want me but didn’t want anyone else to have me either. -Anonymous
Dear Boy who asked me to be his date to a wedding and then left me at the reception for two hours so you could get high.
I was so excited to be your date. Day of the wedding, I picked the sexiest dress from my closet. I wanted you to be sure you picked the hottest date. At the reception, you didn’t pull out the chair for me, nor did you get me a drink. You didn’t seem to care when others complimented you on your date choice. I only danced with my friend and slow danced with your friends because you hide in the corner, drinking wine and texting. Every time I asked you to dance with me, you told me the next song. Late in the night, you came to me saying you needed to give a ride to a friend and would return to the reception shortly. I asked to go with you, but you told me to stay since I looked like I was having so much fun. I would have rather danced with you. I would have rather spent the wedding with you. You returned two hours later reeking of marijuana and trying to convince me you only left for 20 minutes. Not wanting to apologize, you turned the argument on me telling me I was too drunk and you couldn’t believe you brought the stereotypical drunk girl to the wedding. Next time you’re invited to a wedding don’t check the plus 1 option. -Anonymous
Dear Boy who was too cheap to purchase my lunch, but criticized the beverage that I chose and paid for.
We decided to have a quick lunch date since it matched better with our schedules, picking a sandwich shop. You didn’t hold open the door for me nor did you let me go first in line. You only purchased a sandwich and chips, not wanting to spend the extra $1.50 on a beverage. I purchased my own lunch including a diet soda. I let it slide that you didn’t purchase my meal; after all, it was only lunch. As we chatted over our meals, you grabbed my drink to take a sip. You spit it out when you realized it was diet. I rolled my eyes as you questioned why I would choose diet, knowing you didn’t like it. I decided it was best to ignore your text the following week for another lunch date. My diet coke and I would rather have lunch alone. -Anonymous
Dear Boy who I really don’t want as my friend.
After you showed up on our first date, I was delighted to know that the energy you exuded in person matched that of your online dating profile. You were everything I thought and hoped you would be: tender, kind, tall, funny, successful and generous with your ideas of planning “the best first date.” During those three months you showed up consistently, never making excuses, and never faltering with your gentlemen-like gestures of holding open car doors or giving me the jacket off your back. You waited until a yes for sex felt safe and comfortable from me, regardless of what needs you may have had. Our dates were memorable, our chemistry satiable and your kisses ever so sweet and passionate. But as soon as that trip came up and you left overseas for six weeks, it was as if those three beautiful months of what we begun to build were nothing more than a memory which quickly faded. I’m sorry I went back to you a year later thinking things would be different. I am not sorry I met you, though since you’ve taught me what it’s like to be treated like a real woman, only next time with the right man who sticks around and doesn’t expire after the “90 day policy”.
The funny thing is I really, really did like you. I even saw a potential future with you, one that seemed promising especially after I was introduced to your family. But you’ve taught me that love takes time, and building trust is a process. And regardless of what people say and even do, it takes a lot more than a three month time span to get to know “the one”, or even “the potential one”. And although you may think we can remain friends, the truth is I have enough of those already. Ones that continue to show up overtime when I need them the most. So dear boy – in the end I’ve come out on top. Because although I’ve loved and lost, I’ve earned more dignity than I’ve given away. -Anonymous
Dear Boy who didn’t remember our drunken make out.
The boy I met a week after my new job started and thought it would be fun to go out with everyone from work and have one too many cocktails. As we hopped into a cab and you grabbed my face and to have a pretty memorable make out session. Finding out later how wasted you were to not remember it. You made it utterly awkward to be around whenever we would see each other. I’m not going to lie by my surprise of you flirting with me months later in hopes we could be normal again. I must be an idiot to have through that the boy I had a minor crush on would ever man up and actually ask me on a date. I never thought asking a girl on a date was hard, but somehow for you it seems it’s damn near impossible. After getting what I thought was a sober text from you early in the evening, I thought it was your plea to have our first date. Only to arrive to you in your grabby drunken stupor and me yet again falling for something I had made up in my head of you being. Thank you for making it so clear that you are still a boy as you tried to unhook my bra through my shirt as I repeatedly swat you away. You continued to not respect my boundaries and being extremely inappropriate. The main thing I have to thank you for is calling me beautiful. Sober, actually calling me the most beautiful girl you’d ever met …. and then again drunk. -Anonymous
Dear Boy who refused to become a man.
We met in college, and maybe that was my mistake. We became best friends, often hanging out late in to the night, until 3 or 4am, watching Entourage and eating take out. Slowly, you won my heart, though you were far from deserving. We didn’t date right away. I knew better than to hook up with you before we were in a relationship, but I wanted you so badly that I listened to you instead of my heart. And eventually we did date. You finally asked me out after I told you that I couldn’t do this anymore, that I couldn’t continue this pattern. That should have been my red flag, that you would only commit when I threatened to take away something you liked. But I still listened to you, and not my heart. Those 2 years were wonderful and terrible at the same time. I compromised myself for you, time and time again, convincing myself that I wanted to “live free” and not conform to the pressures to get married. But I wanted to get married. I didn’t see the point of a relationship that didn’t have marriage as a possibility. And yet, you refused. You were still in the college mindset of doing whatever you wanted, regardless of what was best for the other people in your life. You were the reason I got drunk for the first time, the reason I had sex for the first time, the reason I became less strong in my convictions, the reason I valued myself less and less. This isn’t all your fault, but you didn’t stand up for me when I couldn’t. You, who slept with my best friend behind my back, because you were both drunk. You, who called me crazy anytime I wanted to talk about the possibility of the future. You, who made me doubt myself. You are the reason I hated myself for so long after our break up. The pain is still there. You didn’t break my heart- you turned it to stone. And slowly, slowly, the self-doubt is creeping away. I’m working on believing in myself again. I have become stronger because of you, but I don’t thank you for it. -Jennifer
Dear boy who keeps making promises you can’t keep.
Two and a half years of a relationship I didn’t expect. If I could go back into the time we met, I would have kept it as friends only. When we first met I became too comfortable being around you. The more time we spent I kept forcing romantic ideas that I wanted that you never thought about. Once you had me under the loop you stopped doing all the productive things for yourself. You stopped impressing me once you knew we wouldn’t end. Somehow I still want the best for you and I. Every time you made a promise that you would change I always believed maybe you would but it was just something you would say just for me to forgive you over and over again. What’s meant to be is not always meant to be. Someday you’ll realize you’re not a boy but a man that needs to grow up. What’s love isn’t love anymore, and only time will tell, and by that time I’ll be gone. Sorry you couldn’t change and I couldn’t hold on enough to make you change. I learned in life you can’t always try to change a person, it has to be that person who wants to change. Thanks for some of the good times and thanks for all of the bad times I will remember. -Anonymous
Dear Boy Who Thought Talking About Other Girls Would Turn Me On.
It started as very witty flirting that made me excited to open my phone. I met you on Tinder, which made me wary, but you shared my love for Archer and you looked so cute on Facebook that I decided to meet you for a drink. You chose a crowded place on Jane Street that took me 2 trains to get to. You were shorter than I thought you’d be. Our conversation (or what I could hear of it over all the noise) seemed forced and you seemed strangely aloof. I wondered if I should have worn heels even though it was snowing. I was sure our first time meeting would be our last but to my surprise you texted me the next day asking when you could see me again. I chalked our uncomfortable encounter up to nerves and decided I’d give you another chance. On our second date, drinks again, you were funny and clever. I admired the fact that you were confident enough to leave your job as an investment banker to pursue a promising start-up and when you kissed me goodnight there were definitely sparks. A few more really fun, really alcoholic dates and I was sure this was on its way to becoming something real. But then, you disappeared. Two weeks passed and no word. I decided to take charge and ask you where you’d been. You replied saying that you’d been really busy dating this other girl, but not to worry! It wasn’t serious. I don’t know why you thought this was the appropriate response or why you were surprised when I never texted you back again (though 4 more texts on 4 more occasions did force me to appreciate your persistence). I don’t know who taught you how to date, buddy, but you should lose their number too. -Gigi
Dear boy who consistently calls me drunk at one in the morning, you’re never coming out the friend zone.
We met at a party at the end of spring semester. You ere cute and a great dancer, but a little too intoxicated for my tastes. We allegedly had biology lecture together (I’m still not convinced) and you asked to study with me for the upcoming exam. When you texted me the next day, I realized I hadn’t bothered to remember what you looked like and told you to come find me on the third floor of the library. I put your name in my phone as “Library Boy”. Three weeks later, we watched a movie at your place when your immature roommates slid condoms under the door and yelled down the hallway all night. A week later, you broke up with me as friends because you didn’t want a girlfriend at the time, but being around me was “just too hard” because your feelings were “just too strong.” I was confused that you thought there was ever anything between us. Like clockwork on Friday and Saturday nights, you text and you call begging me to come make “this lame party so much better”. You’re the one who disowned me, bro. You’re still in my phone as Library Boy, and that’s how it will stay. -Anonymous
Dear Me who seems to never learn from her mistakes.
I’m probably getting into this situation again. I’m urging him to be what my mind wants instead of who he really is. I’m believing there is more to men then just wanting to get in my pants… there’s not. I am settling and thinking it’s okay to do so because I want to be spontaneous and in the moment. Stupid me, desperate me, hopeless romantic me…. stop. Just stop, move on and smile through. You are more and you will meet someone that is worth all the disaster situations you allow yourself to be in. -Anonymous
Dear Possible Man that I really don’t want to screw this up with.
The way we first met is hilarious to me. Back in high school I called you Daddy, because of some family thing you and your girlfriend made up at the time. I’m not sure why you picked me, you explained it to me, but I’m still in the “why me” stage. You are wonderful and amazing, you truly are. I’ve met your family and they are just your normal kind of family. I really like your family. Okay… we both don’t have normal families, but in the terms of normal for us, they are normal. You are a family person just like me, which I really love.In the past months, you have helped me to truly see that not all guys are douchebags. I have had to keep myself from stopping and staring at you with my mouth open wide. Mostly the mouth open wide part, sometimes I can’t help but stare at you. You are sort of a wonder to me. Half of the time I’m not sure what to make of you, or why you couldn’t have shown up sooner, and other times I just tell my brain to shut up and enjoy. I’m enjoying what is going on between us.
I love that you’ve accepted me for me. I love the little things you do for me. I love that you will wear a shirt to bed for a couple of day for me, just to get your sent on it. Than give it to me so that when I’m at home I can wear your shirt to bed and smell you when I wake up. It makes evil mornings a lot better. I love the things you say to me when we’re in bed together. That you have me, that I’m caught, and that I’m yours.I don’t want to screw this up and I know you don’t want to screw this up either. We might not screw this up and even if it doesn’t work out between us, I want to thank you. I want to thank you from the bottom of my heart, for being you. You are simply beautiful, wonderful, and kind. This is just the beginning for us and I can’t wait to see how far and where we go. Well I can wait, because I want to enjoy each day to the fullest with you. -Satisfied
The second half of the Dear Boy letters will be published Monday. There’s still time to write one! Email me.