Tag Archives: ask her out

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.


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,