A Letter to My Best Friend’s Boyfriend...

One of my fantastic readers found herself in the peak of inspiration the other day, while talking with a friend of hers, and she sent me this letter that she wanted to send to her best friends boyfriend. After reading over it and LOVING every bit of insight she wanted to share with this lucky guy, I asked her if I could share it with everyone, because it is a great guide to understanding women.

Take what you will from this letter, but if nothing else, be inspired to reach out to your direct community of friends and family. The more we reach out to each other, the strong our bonds become and the richer we grow, from all the positive vibrations that radiate between us.


(all names and locations have been changed to protect the privacy of the people involved in this story) 

A Letter to My Best Friend's Boyfriend

Dear Nick,

Jen and I have been friends since the day we learned how to read the word “dog”. I mean, we practically grew up together. I was there when she lost her first front tooth in 1st grade. I was there when she danced to “Stop” by Spice Girls during the talent program in third grade. I was the one who accompanied her to the girls’ bathroom the day she got her first period. I was the first person she called after her first date with the sophomore guy she met at the school library and later became her first boyfriend. And I was also the first person she called when they broke up two months after.

I was with her, ever present during those medium-awkward to major-awkward moments of her life. I’ve seen her rise and soar like Boeing 747. I’ve seen her break and fall like Icarus. I’ve seen her fall in love with that guy, and with that other guy, and another. But with all honesty, I’ve never seen my friend THIS happy. No one ever made her feel the way she feels when she’s with you. She need not tell me about it (Yeah, like she hasn’t told me a million times already!). Her eyes tell the truth. The way they glow gives away everything.

You’re a great guy, Nick. You really are. I couldn’t imagine any other guy for my friend. She couldn’t have done any better. I think you two are soul-mates. So to say that I had low expectations from you would be to underestimate my rooting for you dramatically. That is why I am writing this letter to you. If you still find yourself completely flummoxed by Jen’s roller coaster mood swings, immature but coy idiosyncrasies - like how she puts emoticons at the end of every sentence in every text message she sends, and her obvious yet subtle pang of jealousy, this letter would come in handy.

As I’ve said earlier, you are a great guy. But that’s the problem. You’re a “normal” guy. You’re a normal guy who hangs out with the rest of the guys to watch football games while drinking beer and talking about, well, guy stuff. Are you following me? What I’m saying is that whenever you have “girl” problems, you’d probably call up “the boys” and ask for advice from them, and we know where that leads.... So maybe, just maybe, you needed to change the lens in which you view Jen.

Let me lend you my techni-colored glasses, so you can see what I mean. Here are some “tips” on how to deal with her– the 3 things that you need to know about Jen, and about girls in general.

Listen and Remember

Listening and remembering go hand-in-hand. Listen to know her better, and to show her that you REALLY care.

Girls like to talk. You probably know that by now. We like to talk about what we had for lunch, why we chose to wear the linen sweatpants over the pencil-cut skirt, and what made Kristen Stewart the worst Hollywood actress. But we don’t talk just for the fun of it. Talking is also exhausting so no, we don’t like talking like an unappreciated blabbering parrot. But to be fair, and I’m speaking on behalf girls out there, we don’t talk too much. We “share”. We do that because we wanted you to become part of our experiences too. It is an invitation to our superficial cluttered thoughts and someday, if you’ve proven yourself enough, you might just earn your way in the gates of the deepest ones – the thoughts we dare not share a single soul apart from our own.

So the next time she complains about the poor service of the coffee shop where she had her lunch meeting, listen to her attentively. By doing so, you’d know what she liked and didn’t like about the service. She might even tell you her coffee preference. Be prepared for stuff like that. Jot down mental notes and use them for future reference. Remember them when the right time comes. She’d be surprised on how much attention you pay to details so use the information to your advantage. Who knows, you might be preparing her breakfast coffee someday.

Compliment Her

Girls love compliments. Who doesn’t? But we don’t need to hear that we look great ALL the time because we don’t. We’d appreciate it more if you wouldn’t make any comment at all rather than babble meaningless flattery. Seriously.

Now, this is where the tricky part lies. Compliments only work if they are (a) honest and sincere comments and, (b) uttered properly. As a rule of thumb, don’t state the obvious. Don’t tell Jen that she’s gorgeous or that she looks great because chances are, she already knew that when she checked herself in the mirror. Instead, focus on one particular detail that stands out – the thing that made the look. It could be the color of the dress and how it matched her skin tone. It could be the way she pulled of the outfit. It could also be the radiant glow she has that completed the look. It would make her feel more beautiful because the comments are more personal like she’s the only one who has the skin tone to match that color and no one can pull of that dress the way she did.

In addition to that, girls also love hearing “random” compliments. Those unexpected and unsolicited are the ones appreciated more for they sound more personal and sincere. You can compliment her on the way she kept her cool while driving through the one-hour traffic jam, on her choice of food on one of your dinner dates, on how neatly and organized she maintained her planner and some other things you knew she exerted much effort on. But always remember not to overdo it. It defeats the very purpose of the compliment.

So one of these days, when she wears that plain white V-neck top she loves to wear on movie dates, tell her that the shirt looks great with the smile she’s wearing.


Girls need reassurance. It is a standard operating procedure (SOP) for a relationship to work. If she says, “I love you,” don’t say “I love you, too.” Yes, you read it right. DON’T say, “I love you, too.” Well, after what seemed like unending exchanges of I love you’s for seven months or so, we, sometimes, don’t want to hear it anymore. It gets pretty tiring too.

Reassurance doesn’t mean mirroring everything that we say. Because when we say something and it just bounced right back in our faces, we could be better of sending long sweet messages to our own mobile numbers. So do your part and give us more than that without being asked.

Girls tend to over-think and you ought to know that. We can dissect everything you say down to the very last bone, so to speak. Instead of telling her “I love you, too,” use examples of what you love about her, or try to quantify (I’m not saying it’s possible but at least, try) how much you love her. It’s okay to be cheesy and corny if those are what it takes to make her feel secure. It is part of what you signed up for by being in that relationship. And the next time she told you that she misses you, tell her that you wanted to see her so badly, because you just wanted to hug her tight and never let go. You’ll sure win her heart if you follow up with an action. She’ll fall in love with you over again with a sweet romantic gesture like showing up on her doorstep with a fresh daisy that you picked from their own garden.

Basically, those are what you need in order to keep up with Jen’s roller coaster mood swings, immature but coy idiosyncrasies and obvious yet subtle pang of jealousy. Yes, she could be difficult at times. Who isn’t, anyway? So just listen to her attentively and watch out for clues. Make mental notes so you won’t forget to use them to your advantage. Compliment her but don’t overdo it. Random unsolicited compliments tend to sound more pleasing and sincere than plain flattery. And lastly, reassure her by being cheesy and romantic.

Do them by all means and practice them at all times. If these don’t work, I don’t know what will.


Your Girlfriends Best Friend, Annie.

I couldn't have said it better myself Annie! Thanks for sharing!

And to all you readers out there who are LOVING this kick ass letter, if you too have some advice for the world, or for a specific someone, feel free to send me an email at StrategyLifeCoaching@Gmail.com