Category Archives: Teen Issues

The hardest part of growing up is not knowing the rules of the game.

I Like My Friend And She Wants To Date Me, What’s Next?

Dear Rob,
Well I’ve got a problem as everybody who writes to you has got. Let me tell you the whole story.

I know a girl, for something about 3 years, and I always liked her, since the first time I’ve saw her. But, along these years she was always dating… And reading some of your answers I realize I’ve done a lot of wrong things, but it doesn’t matter now, what matters is that now she’s available.

But the problem is that I was always her friend, because I couldn’t be more than it. And even liking her I always date other girls, trying putting her out off my mind, never worked, but I was trying at least.

And now, when I really believe I just forgot her she comes with that and tells me she love me. Not like, love.

And I just don’t know what to do. Because nobody has ever told me that. And because of it, she is more and more present in my life, like sending me e-mails, calling… keeping in touch, and to make things worse even more in one of these flirt times I told that I love her too. But I don’t know if that’s really truth, she is hot but now I can have it, it doesn’t see that huge.

And, some times I just feel like I’m a stupid for don’t enjoy this wave of luck, but I’ve already tried to kiss her when I had the opportunity but I couldn’t, you just couldn’t. And I don’t want to be a mean guy.

So… What should I do? I now it’s complicated, but… What do you think?
P.S.: Just to let you know… You’re getting famous… I’m from Brazil, Rio de Janeiro to be honest. Can you believe it? Internet it’s swell.

Hi Rio Guy,
I would think that your streak of good luck is just beginning.

It’s not all that complicated:
The girl you wanted for 3 years is suddenly available, even tells you that she loves you, and suddenly you’re just not that interested in her anymore.

Happens all the time. The chase was more fun that the winning.

Now that you’re available, she’s available, what is your next step?

Well, you date her. Slowly. Grow your interest with her again.

Moving from the friendship arena into the lover’s room is a big step. So my advice to you is go slowly.

Date her but start with the casual things that you both have done before, now just do them only the two of you. Go for walks, go and have meals together.

Don’t force the relationship ahead too fast. You have a real advantage starting this relationship since you are both comfortable together.

Keep things comfortable.

And avoid talks of past relationships, OK?

If you’re still not sure then I’d come right out and ask her about why she wants a relationship with you.

Put all of your cards on the table and just ask her.

Bare your feelings too. But just enough to keep her talking.

Don’t wussy out again and start trading “I Love You’s” until you’re more along in your romance, if that is where this leads you, OK?
Best Wishes,

Getting Her Interest And Failing To Close

Hi Rob,
Some months ago I got dumped by my girlfriend (we were closed to getting married after five years of living together) for a skinny ugly but rich and charming man twice my age. I was devastated for the months that followed, but when I started visiting your home page and read lots of your advice, I started to feel much better about my predicament. In fact my whole way of thinking (which was rather narrow and stereotypical I hate to admit) changed due to your advice.

I have now fully gained back my confidence and self esteem to the point where I can almost date any women I like. Almost being the key word here…….. I have fallen in love, and deeply I must say, to a cute girl from my job at a big time luxury hotel.
I have showed her how much I like her by courting her with quite some ways e.g. joke/innuendo/compliment/tease combos, body language, etc. After a few days of the above mentioned behavior which she really seemed to enjoy (she laughed, giggled, and smiled the whole time and generally responded in a very positive way) I gave her my phone number and told her to let me know if she’d like to come to work by car with me, since she lives close to me. Her response was a pause followed by a sly smile and tons of thank you for thinking like that.

I didn’t ask for her phone number since I didn’t want to put any pressure on her, but made a really strong pass on her, and judging from her smiles and responses I was almost sure that a touchdown was imminent. To my surprise she never phoned me, and I have the feeling that she is avoiding me. Whenever she is around me she looks very nervous and anxious about something, ignores me, and doesn’t respond to my courting anymore. All she does is greeting me politely and off she goes. WHAT HAPPENED?

I am 28, ok looking, well educated and have experience with women, but my being in love is clouding my ability to feel what happened!
Did I intimidate her? Did she just play with me? Doesn’t she like me the way I do? I don’t know, Rob, help out please!
Mr. P
P.S. I forgot to mention that I am her supervisor, and her uncle is my boss who by the way really likes me. She’s 25 and pretty so she’s had experience with men.

Hi Mr. P,
Let me tell you a story.

There was this guy that wanted to surf.
He bought books and did a lot of research about surfing. He learned all he could about the sport. Types of boards, locations that are good for surfing. Styles of clothes to wear. Everything surf-related that he could find he read or watched or did.
When he was ready he went and bought the best surf board he could afford.
He headed to the beach, waxed up his board, then went into the ocean and waited for the big wave to take him away.

Mr. P, you are that guy, sitting in the ocean, waiting for the big wave to come and take you away.

You’ve done everything. Except you didn’t go and catch that wave. You’re sitting there, legs dangling in the ocean, waiting for the wave to come and get you.

Mr. P, you’ve flirted, you’ve complimented, you’ve shown your interest. Then, instead of closing the deal and catching the wave, you gave her your number and now you sit, waiting for her to call you.

Big mistake.

She knows that there are a lot of surfers waiting to catch her wave. She doesn’t need to go and get the surfer. She doesn’t need to call you, you need to call her.

It’s really stupid to lay all that groundwork then back off by giving her your number and waiting for her to call. You should have gotten her number, not wussied out and given her your number and waited. You should have gotten her number and asked her for a date.

She looks nervous around you because she shouldn’t have to make the next step. She doesn’t call you for a date, you call her. That’s what she knows. It likely seems to her that all your courting, as you call it, was simply a put-on because you failed to close. And now, every moment you see her, that feeling of lost interest is being reinforced because, continually, you are failing to close.

She likes you, or at least she did, but now she’s losing interest because you backed off at the critical moment of getting her number.

The next time you see her, you get her number and say that you’ll call her later that same night to make a date with her. And leave it at that until you call her.

Your call to her will be short, just a couple of minutes long, to tell her when you’ll pick her up. The date should be no more than two days later. Plan something fun to do, not a dinner or anything like that. Build the momentum of dating by starting with fun things you can do together. Maybe your third date can be a dinner. No pressure, right?

The other thing I’d be concerned about is that you’re in a family business, dating your boss’s niece. Be sure you aren’t going against any company policies by dating another employee, especially one that you supervise. You may want to clarify dating her with her uncle because of this, I don’t know the situation.

Stop waiting for the wave to come and get you, make it happen. Swim out to that wave and make things happen!
Best wishes,

Getting With The Popular Girl

Hey Rob,
I have been reading some of your replies lately to some other people and so I figured you would be the only person who could help me!

There is this girl in my high school. I am 16. She looks really nice. We only talked a couple of times, I just know her cell phone number due to some incident that happened to her but she doesn’t even know me too much to talk on the phone. I would end up making a fool out of myself.

The problem is that she is one of the popular girls in school, you know the rich and popular type. Whereas, moi, well let’s just say I am not exactly a looker and to some extent, yes a nerd. Not really one of the richest/popular guys at school.
I don’t even know her too much to know what interests we share… it makes me really sad. Its summer now. I don’t know how I could survive 3 more months not looking at her! Please give me some advice!! I am desperate!!

Getting in with the popular girl at school isn’t all too hard, depending on her overall attitude and availability.
And your self-confidence level.

First off, what makes a popular girl popular:
– She’s good looking
– Hangs out with other popular people
– Clean and nice smelling
– Wears nice clothes
– Knows the lyrics to the top songs
– Enjoys going out with her crowd of people
– Dates lots of guys without getting serious
– Shows that she has self confidence and high self esteem (even though she probably doesn’t and is scared on the inside of becoming unpopular)

She is surrounded by popularity so it just rubs off on her. She has attitude and a level of personal pride. And it’s these things that usually also stop guys from approaching her sincerely, why she ends up dating jerks. It’s the jerk that actually shows confidence and has the ability to talk to her, bust on her, that allows him to enter her social circle.

Now, what makes the unpopular guy such a loser?
– He’s not always dressed well
– Not always smelling ‘shower fresh’
– Doesn’t exude confidence in himself
– Keeps to himself, not very many friends
– Doesn’t get involved in group activities unless he can hide behind someone else’s actions
– He’s a follower not a leader
– He thinks that he’s not good enough to become popular
– Usually very afraid to talk to girls
– Afraid of being told he’s wrong by his peers so he doesn’t voice an opinion about anything

So, if you want to turn around your chances to get with the popular girl you have to make some serious changes about your own personal outlook.

You’ve got to be able to approach, talk to, joke with, bust on, all kinds of women. Not just the pretty ones, not only the popular girls, not the ones that makes you dizzy with sexual thoughts. You have to be able to talk to any girl, any time, anywhere.

You’ve got to clean up yourself so you can break into the group that surrounds your ideal girl. Make yourself into a confident man. Not a lovesick puppy.

How do you start these changes?
– Go shopping. All by yourself. Clothes shopping is the best. You need to find a shirt, a stylish shirt. One that fits well with a high price tag. And you’re going to approach sales girls in the clothing shops in the mall and you’re going to get them to help you, not only find the right shirt but help you to get used to conversations with pretty girls. Go into the shop. See the pretty sales girl. Ask her if this shirt (any nice shirt you pick out) comes in your size. Ask her if she’d date a guy in this type of shirt. Ask her what she has that goes with the shirt. Ask her if she’s seen the latest movie (what ever it is) and if she thinks that a shirt makes the guy in the movie she saw and why. Bust her on the badly chosen character she mentions. Then say thanks, and you’ll think about the shirt. And move on to the next store.

– Get some lines prepared to ask sales girls, waitresses, about what they think, what they do on their job. These girls that are paid to serve you are great to test out your lines and build your confidence. They have to be nice to you. Just remember that they aren’t going to date you, just reply nicely to you.

When you’ve started getting used to talking to women, move on to your target. You’re lucky in that it is summer, so your popular girl likely isn’t going to be hanging around with as many friends as she did in school and may have more free time to spend with someone new. As well, the pressure is lessened on her to be such a tight-ass popular girl and break on the geeks and nerds. Your chances are better during summer vacation and holiday time off school than any other time during the year because of the less pressure to maintain her status quo and the popularity pressure from her circle of popular friends.

You’ve got her number. Call her up. Say you like her style sense, meet me in the mall tomorrow and help me buy a shirt. Don’t ask, tell. Give her a time get her to say yes and get off the phone. If she says she doesn’t know her say you’re the guy that did that thing with that other girl that so many people talked about. Don’t describe any more. Get her interest up and get the date when you tell her when and where and then get off the phone. 3 Minute call, at most.

When you meet her at the mall go into the same stores where you started conversations with the sales girls. Hopefully you’ve left a positive impression on them and they’ll treat you really nice, maybe even remember your name. This is a great way to stir interest and maybe spark a little jealousy in your popular girl, making her want you just a little more.

Be prepared with small things to talk about:
School classes

Get her to talk about herself more than you talk about her or yourself. Do not allow any awkward silences. If there seems to be a break in the conversation, jump in with “What do you like about…” and keep the conversation going.

This should get you going. You’ve got your work cut out for you now.
Best wishes,

Playing The Ignore Game

Dear Rob,
I’m sorry for emailing you, but I asked you for advice before and I thought I would try again.

Well I’m not sure if you remember…but my case was the one where this boy who is 23 and I’m 22–well to cut a long story short… he was the guy who would always ignore me… since I ignored him…

Well to continue on from what happened from the last time I emailed you… Well I tried to go up to him and to show him that I liked him and I think he was a bit bitter or something since he just acted like I did not exist even if I went right up to him. Well I tried for about a month and on my last day he brushed past me and acted like I never existed… I got tired and thought I’m tired of this. We had two months break from university. And I decided to move on… stupidly I found out his name and what he likes and found out we did out first degree at the same university…sometimes I wish I never knew this either…

Anyhow, these past two months I tried my best to forget about him and I had a hard time from other problems I was having. Anyway, everyone kept telling me…oh…he ain’t interested… since guys don’t ignore girls. And that made me more determined to “move on” (wring use of words–since nothing happened to move on from) but anyhow, when I went back to university I saw him at the bottom of the stairs. I acted like I never saw him… which was easy to do… and he was talking to this girl and laughing… and when she was going pass me… he came and walked towards me. He opened his mouth I think to say something. I was just so angry for some reason and had so much on my mind from exams etc., that I just pretended like I never noticed and walked off.

Well for weeks he disappeared–usually I would always see him in the library and nothing. He just seemed to have disappeared.
I saw him accidentally one evening coming out of his department. I for some reason couldn’t help but stare and he stared as well and walked off. Well 3 weeks passed again nothing. BUT NOW we are coming towards the end as in this is my last week and his.

And for a week I saw him about quite a few times and he acted so normal. I would be chatting and laughing with my guy friends and he would come with his mobile sit where I could see him and he would act like I never existed. Again.

Well anyway… I think he knows what time I finish class and this Wednesday I never went class but waited outside the department and he came down with his friends from lunch the usual time I would leave class…purely coincidence. And he saw me and I saw him he stopped few times and acted like he never saw me…and I did same… I waited about 30 min and went in the library where he had gone previously. I walked past him and sat quite a bit away from him and he got up after I sat down and he got up to leave. He had his back towards me at this stage and he was walking towards the door. He stopped before he actually left desk and turned back and we both looked at each other

Now, all my friends say he has “moved on” and is not interested and its time I did the same.
But I can’t feel that he is probably going through the same phases he went in before and now that we are coming to an end of the year and this is it, I think maybe he still has some sort of interest.

Am I reading to much into this? Has he moved on? What do you think?

Hi M,
It seems to me that, so far, no one has made any forward moves. You’re both still playing this “I see you, now I don’t” game.

You have a choice:
The next time you see him, walk up to him and say “Isn’t about time you asked me out?”
Do as your friends say and move on.

This has gone on long enough, don’t you think?

One of the hardest things for men and women to do is be able to “initiate contact” when they’ve never been taught how to approach others that are not in their circle of friends. After all, how do you reach out to someone that is cute, good looking and probably (as you think) better than you and just going to reject you anyways?

It’s tough, confusing and very hard to prepare yourself to make that first step beyond the distant flirting that goes on when you’re so afraid of being rejected. When your self-confidence is so low.

The reality is that life is full of rejection and disappointment. Another reality is that people play games.

They exert their power of attraction just because they can. Because you showed interest. And as all of this is happening your interest in them rises, you like them more and more since they did show you some initial interest, enough to make you want to want them, then they back off, playing this ignore game.

Get ready to make the move. Prepare yourself for rejection and invite him for a coffee the next time you see him. You may just be pleasantly surprised that he does go with you. And at the very least you will have a definite answer about dating him or “moving on” and getting back to normal.
Best wishes,

College Freshman Dating A Highschool Senior? Not Likely!

Dear Rob,
I recently confessed my affection to a guy friend of mine and to my surprise, he felt the same.

We sat and talked, discussing if we wanted to become more than friends. He suggested that we go on a date, to see where we could take things. So we go out and things are going great. When people ask him if I was his girlfriend he tells them I am. But we get back to his car, we start to discuss our relationship in detail and he reveals to me that he is unsure about us because while I’ll be starting my senior year in high school, he’ll be starting college at a school an hour and a half away from me.

I started to become frustrated with him because he keeps telling me that he really likes me (even mentioning examples) but how he is somewhat swayed by “outside forces”.
He is a very smart guy and a very logical thinker. That’s why he’s had so much trouble deciding. He begins to tear up because he “doesn’t know what to do.”

We decide to leave and head for a park to walk. So while he’s driving, I tell him that I’m sorry… that I shouldn’t have put all that on him but it’s just I have such strong feelings for him and I’ve heard the “long-distance relationship insecurity” thing before.

We both start crying and he tells me that he’s sorry too and I admit to him about my past relationships and how they never seem to work out and he tells me that any guy that wouldn’t want to go out with you is crazy. So we get to the park and talk and have an amazing time. We come home, kiss, embrace and I tell him that I want to see him before he leaves. but since that day, I haven’t received any communication from him although I see that he checked my myspace page quite frequently after our date. I told him how I felt about the whole thing but I haven’t talked to him since. I’m trying to give him his space but it’s coming down to the wire. And I really care about him but I don’t know what to do. I feel emotionally exhausted about the whole thing. 🙁

Thanks for reading. Hope to hear from you soon. 🙂
Hopeless in Colorado

Hi Hopeless,
This guy doesn’t need his space. He needs his life. And what he fears most is that he’s going to be a college freshman dating a high school girl.
Trust me, it’s not going to work. There is distance and the school bias working against this. Your guy knows this although he also knows what he’ll be missing if he doesn’t date you now.

He’s already showing you his doubts and, with distance and a new life and the college world in front of him, your relationship won’t last if you let it get started. And he’s ignoring you so that he doesn’t have to say this to your face.

Remain his friend but know that your lives are about to take different directions. Do not get involved at this point. If he asks you why you’ve decided to remain friends tell him what I told you.

And next summer, should you both be single maybe you can really become more than friends. But not before. Too many changes are going to happen to him, and you, in the coming months.
Best wishes,