Tag Archives: teen love

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.


How Do I Get Her To Go Out With Me?

Dear Rob,
I am 18 years old and have recently moved house with my parents (about 11 weeks).

I have been hanging around with my cousin and making new friends through him and the circle kept growing until I met a girl of the same age who I have a crush on and now I see quite regularly as she is also close friends with my cousin.

We text and chat a lot but it always seems too ‘friendly’. But occasionally she will text me if we haven’t seen each other in a while just saying “Haven’t heard from you in ages lovely……..hope your ok…….haven’t seen you in like years” but when we talk it never seems a serious conversation. it will always end up joking about really random stuff and text laughing (hahahahaha).

We have a lot in common and laugh about the same things and I am always showing her that I care for her but I feel like she either hasn’t noticed or she has and is hiding it – I’m finding it really hard to work her out and I don’t want to leave it too long before I tell her I like her because I know that there are other guys interested in her too.

Please can you help me? I’m in a pickle?
Much appreciated Bob

Hi Bob,

She’s patiently waiting for you to make the first move. Really.
It takes a girl about three nanoseconds to decide if you’re worth the effort… clearly you are and she’s giving you all kinds of chances to ask her… so make the effort!

Stop playing the “let’s be friends” game while she is clearly interested in more otherwise her attentions will be turned to another guy because you haven’t “made a move”.

So, the next time you see her you say to her:
“Hey, let’s go out, just the two of us. You can take me on a date where ever you like. But I’m not a cheap date so make it a nice place!”

And stop constantly being available to her. You’ll become too much of a friend and not enough boyfriend material. No more instant replies, no more being always available… until you get that first date.

Don’t turn all wussy on her (or me). Be The Man that she wants to date. Add some cockiness and some mystery to your behavior and you’ll be fine. You’ll get the girl!
Best Wishes,