Category Archives: Teen Issues

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

The Classic Ignoring Game

Hi Rob,
Recently me and my ex-boyfriend have been talking to each other again and doing some casual flirting.

Our first break-up was not very good (I broke up with him) but somehow we were able to pull our friendship back up, we were really close friends before we started dating. Over the summer we thought about getting back together but for some reason it didn’t feel right to me (chemistry?).

We had gone to the movies over the summer and it ended with a kiss and even though he sort of asked me out (he mentioned the fact that he felt it was implied over the internet that night on IM, I begged to differ) I didn’t go back out with him. Nevertheless after a really big fight, and a rough patch we were able to casually talk again.

In October when we had no school he came over to watch a movie and we ended up making out. It didn’t go any further than that and he was still extremely sweet.

He joked around a lot with me, spun me around in circles in my room and even gave me a piggy back ride downstairs. Now he isn’t the football type guy who gets all the girls and does the one-night stands. In fact I’ve been his only girlfriend, and he’s generally speaking a really sweet guy, although I know that he has a tendency to emotionally shut-down sometimes.

Anyways we talked a little bit after October, nothing too serious, and then we started talking a lot in January.

There would be some nights where even though it was a school night we’d talk till 2am or 3am in the morning. In one of these late night conversations he said that he was still very much attracted to me but wanted to try branching out a little (dating other people). After one of our really late night conversations we decided to keep texting during school and then later that evening he just stopped talking to me. Now he’s ignoring me. He helped me a little bit with an internship application but then after the application was done he stopped talking to me again.

My sweet 16 is in a month and I asked him for his address to mail the invitation letting him know that of course he didn’t have to give it to me if he didn’t want to come, but he still gave me his address even though he decided not to continue the conversation past that.

In the midst of all this ignoring, I’ve been subconsciously thinking about him more leading to point where *I* actually like him, but he’s still ignoring me – holding all the cards almost. Any advice? I feel like I’m getting mixed signals from him and so I don’t exactly know what to do even though I would really like to go back out with him. Please help.
Thanks Rob.

Sorry to say but you’re only the “last boat in the harbor” as far as he goes.
When a guy says “I want to branch out and date other people” he really means is that as long as you’re available he will make out with you, and maybe look for more, but you’re only ever going to be a friend with benefits.

His ignoring you is the biggest sign that he only wants you when he wants you, nothing more.

Stop expecting him to change and you’ll get over him. Find another boy, I bet you have plenty of choices if you only look around, or enjoy your ‘singledom’.

I hope this helps,

Asking Out Advice

Hey Rob, I am 16, and I’m a junior in High School, and I met a girl a few months back that I really liked when I first saw her.

She is 14, and she is a freshman. I’ve always liked her, but I’ve never talked to her that much.

We are both in the band, which is how I met her, so we see each other around 12 hours a week between practice and football games and what not.

I’ve always tried to be nice to her, and help her with anything that see appeared to need help with. I’m very shy though… so I don’t talk with her much.

This Saturday is possibly the last football game (last thing this season) of the season, so if our team loses, I may never see her again. I probably won’t see her because freshman have a different school building than upper classman. (Go our team!) I wanted to ask her out a long time ago… and I keep telling myself that I will, but I always find some stupid reason not to.

I don’t really have high levels of self-esteem… though I can’t say that i’m ugly or fat, I just don’t have confidence when it comes to people… especially girls.

I’ve done some internet research on her… not that I want to be creepy… but I found out that she would most likely like movies. She also plays guitar, like me.

Anyways… everything i’ve read on the internet about asking girls out say you need to be friends with um, and I’m pretty sure she knows my name, and I know she sees me around a lot, but I never talk to her, and I’m pretty much out of time.

Oh and just to throw this up… so you kind of know what I know, she does hang out with a lot of girls, and i’m 95% sure she does not have a boyfriend because I never see her with guys.

So what should I do? I really like her a lot… and I want to go out with her, but I don’t know what I should do.

Any advice would be much appreciated.


Hey, it’s OK to admit that you’re having a hard time to get the steam up and ask a girl for a date.
Totally natural.

But you need an “opener” so you can go farther that the few words you’ve said to her.

Ask her to play guitar with you.
This is your way to asking her out.
Casual. And something you share.

And I’d bet that she’s just dying for you to take her to a movie, or to see something in your city. Together.

You’re not creepy, just unskilled… which is good.

Start by asking her for her email…. Instant messenger.

Easy peasy stuff.

Don’t be your own blocker, you CAN do this.

Shut down the scared little man inside you. Know that you are ultimately not controlled by fear… and that she desperately wants you to move forward.

Good luck!

A Man Has To Have A Plan

Hey Rob,

I am 17 years old and I met this girl about a month and a half ago.

We really hit it off because we have pretty much everything in common.

After a little while, we both got into whether we like each other.  It turned out that we both liked each other a lot and things were going great.  This girl means everything to me right now.  It’s a different feeling than with other girls.

I don’t want to get into sex or anything, I would rather just hold and kiss her.  Anyway, I eventually asked her out.  She was very excited but realized that she couldn’t “bring herself to date”.

What the heck does that mean?

She says that she needed some more time and has to straighten some stuff out.

Well, it has been a matter of weeks now and she still does not want to.

I am looking for a relationship in my life right now and do not know whether to wait for her or to try to move on.  Pleasseeeee help me with this!


This is a classic case of being too friendly with her and she feels that you’ll be smothering her if you’re around more.

Take a break from her… make her wait for you…
When she calls, emails, messages… ask her if you can call her back, IM her at a later time… and tell her a later time, be specific… you want her to be waiting for you.

I bet the two of you have done a lot of “hanging around” but you haven’t planned anything to specifically for the two of you to be together and do something.

A Man has to have a Plan.

Step being so available to her;
When you get together have a plan on what to do;
And talk to other girls.

One of the best way to increase the attraction of the one you want is by gaining the attraction of another and making her jealous.

Good luck!


How Teen Men Start Dating

Hey Rob,

I’ve just been looking through your advice central and have found some of the stuff really interesting. However, I’m not sure how relevant the stuff is for me.

Now, I may have never had a girlfriend, but I am not shy of girl, generally. I occasionally get a bit flirty just to sort of… Dare myself I guess. I get very flirty with the girls I am closest with.

One girl in particular I am constantly hugging and holding hands with in lessons (However, she is WELL know for flirting with guys, however she does seem rather more than usual with me). We talk constantly. I have found myself coming so close to asking her out, but I can’t… If she said no, it would make our friendship very awkward.

I’d also feel very embarassed all of the time in school and so on.

The other problem is there is another guy like me in the year below who she spends her break and lunchtimes with. She is just as flirty with him as with me (Me and him are good mates actually). I always feel incredibly jealous when they are near each other. I really don’t know what to do…

My other issue is that I have feelings for another girl. I don’t know her as well and have only started talking to her for about a year. I try to talk to her, but I try not to make it obvious I like her. In fact, I try to make out as if I’m not interested in her sometimes. I’m very careful with what i ask her or talk to her about. She isn’t as pretty as the other girl, but I like her personality a lot more.

The big issue is that I am not friends with any of her friends (except one). She is popular, especially with a group of the “tough” lads who don’t like me.

When I talk to her as of late, I have found myself insulting her as a joke. I try to make it very obvious I’m joking so it seems like flirting, but I’m not sure if she realises, or if it annoys her, or anything. in fact, I’m probably being stupid by doing it, I’m just not sure.

If I had to pick which girl I could have, it’d be the second, but I doubt I have a chance with either…

Any advice greatly appreciated, thanks rob for taking the time to read this.

(I don’t which to give my real name in case any of my friends see this if it gets published!)

Thanks, Anonymous


The fact of the matter is:
1 – you have to decide who to ask out, and
2 – you need to stop being a wuss and ask one of them to “help you study” or something where you can spend time alone with her, whichever one you choose.

Stop being a flirt, that only works for so long. It’s good to have girls that are friends, but it’s better to have a girlfriend and you know this or you wouldn’t have emailed me.
It’s time to take responsibility for your feelings and act on them.

Plan your next move with the one you really like and if she breaks your heart, well, that’s just one more step on the walk of life!

We all have confidence issues when faced with starting to date, it’s natural, awkward and totally realistic. What you have to do is allow yourself the opportunity to “fail” with the one you like so that you will know how to handle this later in life. If you keep hiding your true feelings you’ll never do well with women.

Ask her and maybe, just maybe, she’ll say YES instead of NO.


Has She Lost Interest?

Dear Rob,
I’ve been enjoying your advice and think you have some great opinions
to offer so here goes.

A girl started a 7-week internship at my company recently and we hit it off right away. After a couple days of work together, I gave her my phone #, which she thankfully accepted. She didn’t give me hers in return claiming she doesn’t “give her number out to very many people” to which I replied with a shrug and a laugh and said “we’ll see.”

That same week, I invited her to play some tennis after work; she said yes and we ran around for an hour chasing tennis balls, having a great time, and flirting the whole time.

The next week the subject of favorite foods came up. I found out hers is Thai, as is mine, and so I asked her if she wanted to go eat some Thai food. She responded “I’m trying to save money right now,” (she is paying for college credits to work somewhere for free-I still don’t understand how they get away with that-and gearing up for a European vacation) and so of course I offered to buy. She said she didn’t want to do that because she’d feel like “she was taking advantage of me,” and so instead of pushing it I just said OK. That same night, she text messaged me (giving me her phone #) wishing me a great weekend because I was leaving for the weekend the next day, and also saying she thought we should go out for Thai after all.

We went out the next week, had an amazing dinner, found out we have the same or similar values, passions, and center, so to speak, in our lives and it was great. She made it a point, though, to tell me that “this isn’t like you taking me out, you’re not paying for me, I’m here because I want to be here.” I guess you could say she threw me a major curve ball.

Here’s where it gets interesting. The next week, she invited me to ride with her to the town her college is in. She had to go up for an evening to help plan some events for her upcoming graduation. It’s about an hour away from where we work. I have friends up there and she knew this, and so her thought was we could ride up together and while she did her school thing, I could hang out with friends and then we could ride back home together. We had a great ride up, had time for pizza in the park, and then after she was done, she came over and met some of my friends before we left. It was a good night.

The next night, we went to a football game together, got take-out, went back to my house, watched a movie, and flirted the whole time. It was a good night. Other than halfway laying on each other and that sort of thing, it never got physical. Also, the subject of our relationship never came up and I never made a point to bring it up. I thought it was becoming pretty obvious we both liked each other. And, since we work together, I’ve been hesitant to move too fast. I didn’t see her the rest of the weekend because I was at a bachelor party (no strippers or anything like that, just guns, meat, beer, and competition-that sort of bachelor party).

This last week was her 6th week and it was an awkward one. I felt like she was annoyed with me all of the sudden. Where before she would pass by and smile, it was like she was ignoring/avoiding me, going out of her way to not walk past me. We had a dinner and movie at my place scheduled for Wednesday. On the day of, she insisted on inviting another girl we work with to come over too. The girl is here from overseas and doesn’t know anyone and so I’m all about having her over, but all I got from it was “I don’t want to be alone with you.”

I asked her if we could do coffee and talk this morning (we both have the day off from our job together but she works another job in the afternoon). I figure it’s time to be completely honest with her and see where she’s at. She said she was still in bed and wasn’t up to it before work but “if you have something you want to talk about, we’ll find a time.” What should I do? Should I wait and talk after this next week, her last week at my company, is over? Why the change in attitude, especially after initiating the car trip and the dinner? Did I miss my window? I just don’t get it. Let me know what you think man, I’d appreciate your advice. Wow, this is long, sorry about that Bro.
P.S. She’s 21 and I’m 24. We both do basically the same thing.

Hi Confused,
The easy answer is that, yes, you missed your window.
She was open to your advances and you didn’t advance far enough.
From what you told me she was playing it slowly, making sure you weren’t a player and her attitude became more serious with you when she took the ride with you to her college, you both did your own things, and shared the ride home again.

After that you should have turned on the heat and gotten serious with her. Now, she may be past what she felt for you, figuring in her head that she imagined everything and you’re not that serious after all.

How to become serious after her starting to lose interest?
That’s a tough question.
The answer is harder.

In your current situation I don’t think that you want to let her get away. Make your move on her last day with your company. Invite her to dinner, make it special. You’ve both shared time together, now it’s time to share some romance.
Simply, this is the way to accomplish setting the scene:
Order a dozen roses to the restaurant where you make the reservations and call the restaurant to expect the delivery and have the flowers on the table before you are seated. She’ll see the roses and know what you’re feelings are, unmistakably.
This will be the “make or break” moment, but I’m sure you’ll pull through, no matter her response.
Best wishes,