Advice Column: How To Stand Out When You're The Girl In The Middle

Advice Column: How To Stand Out When You're The Girl In The Middle
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Marco Lastella

Dear Chelsea,

I've been best friends with this girl Ashley since elementary school but we've grown apart a lot since college. I made new friends here at home and she's always been pretty popular wherever she goes. She's the type of girl who HAS to have a boyfriend or a fling. She'll date a guy for a few months, say she's "bored", dump him, and then hook up with a new guy that night. I've never known her to be single for more than a month. She's been like this for quite some time.

I made a pretty good friend, Nick, here at home. We met while working in retail and then reconnected a few years later. He's a great guy and he asked me on a date a few times but I never wanted to because I wasn't fully over my ex.

So Ashley comes home for school break and meets Nick. Naturally she wants him even though it's only been a few weeks since her ex, Brian, dumped her. She asks Nick to hangout without telling me even though I introduced them to each other. I told her I didn't want her showing interest in Nick because I may want to pursue a relationship with him. She basically told me off and said I had no right to tell her what to do.

Ashley is a tall, skinny, blonde so most guys wouldn't turn her down. Nick is into her immediately and falls head over heels after hanging out with her a few times. I tried explaining to him how she is and how she treats men, but he just became angry with me and told me not to say anything bad about her. It came to a point where we stopped talking for a few months.

Well she ended up cheating on him with Brian, her previous boyfriend, which I warned him she might do. He was devastated. Blocked her phone number and all social media. He hated her following their break up and we finally got back to being close again. Nick admitted I was right about her. It's been about 3-4 months since this happened.

Now I find out that Ashley and Brian broke up and Nick is trying to pursue a relationship with her again. I just don't understand and it makes me so angry that he wants her back. She cheated on him and when I try to talk to him about it becomes very mean and defensive. He actually asked me to stop talking to him. I just want to know what is going on and what I should do. Ashley has always gotten whatever she wanted and she's very manipulative when it comes to men. I just don't want Nick getting hurt again.


A Worried Friend

Brooke Cagle

Dear A Worried Friend,

Is it really worry that you are experiencing, or is it regret?

Are you worried for Nick, or are you worried for you?

Are you worried that he will be taken advantage of again, or are you worried that no one will see the advantages of dating you?

Instinct tells me that at the heart of it this concern you have for others is really a concern you have about yourself. Your concern all falls back to you. The fear—even the sadness—of being pushed out time and time again, of being overlooked, chosen until someone better comes along—like a tall, skinny blonde named Ashley.

I know you think Ashley fools men into trusting her, that she charms them with her looks. Do yourself a favor then, and don’t you be fooled into focusing on those looks of hers. Don’t disempower yourself by assuming that what she holds over you is beauty, that if only you were a tall, skinny blonde Nick and Brian and the busboy would all be after you even if you cheated and disrespected them each.

Bypass that bullshit now, the long legs and silky hair. Learn to do away with it early on. Learn to focus on the person not the persona, their character and not the envy or disdain or self-doubt that their image provokes in you.

My advice is, judge yourself against yourself.

And if you feel so compelled to compare yourself to the Ashley’s of the world, compare yourself to the person, not to the looks of them.

I’m a tall, skinny blonde and honestly while this may turn a few heads, it’s never been enough to get a man to dive into a relationship with me. I mean it, a woman’s looks can bring a man to a dinner table, but they won’t make him talk for three hours.

You are the reason he talks, the reason time slows and he explodes with words. And this happens not because your lips are juicy and your curves are insane and you know exactly when to flip your hair and how to send a shiver down his spine. No, men who become invested are investing in more than that, they are investing in you.

A real man commits not because you’re seductive and beautiful, even though that’s nice, but because you speak to who he is when the costume is off and no one else is around. And guess what, that isn’t just nice, that’s important. That’s what will make you special. Not your ability to turn heads but to see someone for who they really are.

This goes for us all. We fall genuinely in love with the person who lets us be, not the person we have to pretend and perform for. We fall in love with the person we can relax around, not the person who makes us wonder if we’re even good enough.

My feeling is, a guy that’s going to be enough for you is never going to feel like a woman’s looks are enough of a prize to commit to. And I think that’s a bit of the rub here. If you were honest with yourself, seeing how Nick is with Ashley actually makes you think less of him which sucks since how he was with you made you think more of yourself.

My feeling is, you don’t want to see Nick lusting after the superficial because you want to think his desire to date you was substantial. You want him to do smart things because that means asking you out wasn’t just done on a whim. It means he thought it through. It means you meant something. My feeling is, you want him to take things seriously because that means he took dating you seriously.

Basically, the sense I’m getting is, you want Nick to be more than he is right now. You want him to be more discerning, more self-aware. You want him to clean his hands of a cheat, to think more of himself than to wade in those waters again. You want him to walk away from a tall, skinny blonde not crawl back to her. When he says he hates Ashley, you want him to hate Ashley. Not forgive her. You want him to not change his mind.

That’s what you really want. Not Nick specifically but proof that a man won’t just change his mind about you.

That’s always been my biggest fear, by the way. The fear that a man will suddenly change his mind, that men will always change their mind about me.

I never knew where this anxiety really came from. Sure, I have an ex who was crazy about me in the summer and made me feel forgettable in the fall. That was torturous. But it was also specific to him. (He was an avoidant addict, perhaps you know one yourself.) Not to mention I had this fear of mine long before he flipped a switch on me. So what caused this insecurity of mine? It wasn’t that I changed my mind easily about people, so I knew others could do it too. I never change my mind about anyone in a flash, and my feelings about someone doesn’t change in an instant either.

After years and years of the answer going completely over my head, I was walking through the airport, my old marching ground where I used to sob and sob after saying goodbye to a boyfriend, worrying already that I had done something to change his mind about me or now that I was out of sight his mind would change about me, well, it hit me two weeks ago right there in the airport.

The reason I’ve always been so afraid that someone would change their mind about me was because I constantly changed my mind about me.

One moment I was proud of myself, the next I was ashamed that I wasn’t doing enough, that I wasn’t becoming enough. One moment I’d feel like my own best friend and the next moment I’d pop a pill that would take me as far away from myself as possible.

I think you may be a little bit like me.

Rajdeep Kataki

I think you’re regretting not going on those dates with Nick because you think that would have kept him from going on dates with Ashley and would have kept you from discovering that he could change his mind about you.

Complicated, right?

I think the fairytale thinking is that once we find a man who doesn't change his mind about us that will inspire us to not change our mind either. But take it from me, the most loyal man in the world won’t keep you safe from the criticism you have of yourself.

Nick’s feelings about you will not free you from your feelings about you.

And honestly, I feel like this is what your letter is really about even though you aren’t addressing it.

How can you feel better about yourself? What do you have that someone like Ashley may not have? What will keep a man invested in you? How can you show up for a man as a friend (and a potential love interest!) without getting the boot?

These are the questions that are calling out to me.

My advice is, learn to talk only about the people who are in on the conversation. The people who are there and listening will respect you for this. They will also think more of you. You see, when you talk about others, like Ashley let’s say, people don’t hold on to what you’re saying about Ashley, they hold on to the fact that you were talking about her, that Ashley is somehow important enough to be the topic of conversation. In a sense, she becomes more intriguing.

Wild, I know.

But it happens this way. People are less likely to remember the content and more likely to remember the context. They’re more likely to remember your capacity to break someone down rather than build them up behind their back. And I get it. Trust me. I understand that you were trying to build Nick up. You were trying to look out for him and say, wake up, you deserve more. But instead of talking just about Nick or just about your experiences with him, you brought in Ashley. You put her down to raise both you and Nick up.

Only you know what that does for Nick? It reminds him things didn’t go according to his plan. It reminds him that he’s acting a little hopeless. That he’s got his thinking all wrong. That he’s in the weaker position. That he’s got the disadvantage. Mainly, by stressing that you were right about Ashley and he was wrong, it buries him in humiliation and makes him want to prove himself which evidently feels more like a desire to prove you wrong.

Trevor Paterson

My advice is, don’t try and teach Nick a thing or two about women. Instead, lend him an ear when he’s ready to teach you about all he’s had to learn for himself. Give him a chance to figure out what he knows. Don’t interfere with his or any person’s heartbreak. Don’t try to speed up their growth. Unless someone asks you questions or says they are willing to hear you out, be a soundboard for them. Be a confidant. The person who doesn’t judge them for what they’ve done, what they’re doing, or plan to do. And by the way, pointing out that this person or that person isn’t right for them is, in fact, judging them. It’s too much direction. And, unless they are asking for it, men don’t like that. No one does.

A man will want you around if you make him feel acceptable. One way of doing that with Nick is accepting that he explored a relationship with Ashley, and may wish to again. Yes, that might be hurtful which is exactly why Nick may not be right for you. Again, right now, he might not be thoughtful enough. He may not see where you’re coming from. He may not even care to. But don’t rule out the possibility that he doesn’t know where you’re coming from because you haven’t spelled it out clearly.

If you want to be an asset to someone, provide them clarity before they even realize they need it.

If I were you, I would be simple and honest and I would talk only about myself. I’d tell Nick something like this:

I’d say that I initially didn’t want to entertain the idea of dating you, not because you weren’t my type or didn’t appeal to me, but because I was getting over my ex and knew that bringing you into that wouldn’t be fair. I knew I wouldn’t be able to go all in and you’re the kind of guy who I’d want to give all my attention to. That said, when you began pursuing my friend, I was just hurt. I guess that might not have been clear to you since from the outside it may have seemed like I turned you down or something. But I guess I was just waiting until I was in a better place before telling you I was interested. The thing is, you going for my friend so easily makes me feel like maybe you weren’t all that interested in me to begin with. I’m sorry for prying or overstepping boundaries by throwing my two cents into the mix. The truth is, I just wish things hadn’t paned out this way.

I believe the best thing you can do in life, for yourself and others, is be open and absolutely transparent about what you’re experiencing. It’s important to talk about your confusion, about all those questions that are wound up so tight within you. It’s important because talking about our confusion is the very thing that clears it up. When we know why we are feeling a certain way, we don’t have to put it off on others. We don’t have to look to the Nick’s and Ashley’s of the worlds to change their tune in order to change our stride.

If you want your relationships to change, first find out why you are really focusing on whatever you are focusing on. Think less about what losing someone means and says about you and more about what you thought you'd gain from having that person. Often that answer reveals so many of our secrets. The truth is, we use people to feel better ourselves. Heck, we don’t even have to use them to feel better. Sometimes we use each other just to feel different.

Life will be easier if you can understand why you reach and cling for others. If you allow people’s problems to be their problems to solve. If you invest curiosity in your own issues. Life will reward you if you stay in your lane.

My advice is, listen to a man but don’t be in his ear. Big difference.

My advice is, rather than sharing your opinion of others, share yourself with others.

Learn more about yourself and then talk from that place. And when it comes to the tall, skinny blondes of the world remember that the long legs and shiny hair might very well be what a man sees but, given time, it’s never “what he sees in her.”

Peter Sjo

Human beings fall in love with conversations. This is what I know for sure. The more honest you can be in your conversations, the more your value as a person will go up.

So, focus on that. Focus not on the looks you may or may not have but on the way you make people feel when you are around them. Focus on what you can say, on what you can reveal, that will connect you to others, that will make them feel acceptable, that will make them feel more like themselves and may even make them feel better.

It might not seem like this right now but this is why real men stick around. Because they value the way you think and what you have to share and they love how you bring their own words to light.

Focus on how you can be better at that. Focus on becoming comfortable with yourself and then watch how others become more comfortable showing themselves to you and sticking around once they do.

And in the midst of all this internal blossoming, don’t lose sight of the big picture, that early on in dating we tend to put too high a premium on those who can lure a man in left and right—we tend to want to be her, we tend to want to do that—but as we get older our eyes open to the women who can get a man to stay, who can get a man to invest, and that is far more powerful than turning heads or taking men to bed.

Trust me, the best thing you can do for yourself is let Ashley be Ashley.

Let Nick figure out Nick.

And let go of your worry.

Every time you compare yourself, your forget yourself. And you, my friend, are worth more than you even let on.



A Breakup Coach trained and certified in Solution-Focused Life Coaching, Chelsea Leigh Trescott helps her clients turn their sob stories into silver lining breakups. Seeking advice? Send situation and question to for a chance to be featured.

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