Tag Archives: will she date me

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.


Will She Become My Girlfriend?

Dear Rob,
I’m a 17 year old guy, and I like this girl. The problem is, I don’t know if she just wants to be friends or does she like me the same way I like her.

Here is some background:
She doesn’t have a lot of “girl” friends, most of her friends are guys. I started talking to her about a month ago at school. She was in a past relationship for 8 months until they broke up. But then they got back together for about 2 days and split again, and I think its for good this time. Well anyway we talked for about two weeks before going out to eat together, and we have been to dinner a couple times after that.

On Fridays I go pick her up and go hang out with my friends. Sometimes we will all go and get something quick to eat. Well, my friends sometimes like to tease me, so we were all in line about to order our food when my buddy ask me, “You paying for your girls food right?”, and when he said that, she said very snappy, “I’m not his girl, there is nothing going on between us”. And I was kind of confused because I had thought we were “dating”. Also, sometimes I will do something nice for her like bring her a biscuit in the morning before school starts, buy her a drink if she has no money. And she will say, “You’re so nice, I’m glad your my “friend”, or something to that affect.

Now it has been about a month since I first met her and we are hanging out more than ever. She invited me over to her house to eat dinner, and she goes with me about everywhere. She calls me every night and sometimes in the morning as I’m getting up. She is always talking about how much we have in common, and how were almost like “brother and sister” (I don’t know what that means). I’m tired of having to correct people when they call her my girlfriend. I like her as a girlfriend, but I’m confused of how she likes me.

Thanks for your time Rob,

Hi Me,
It’s obvious to me that you haven’t yet had a girlfriend.

So this is what you do… stop talking to her. Not in a mean way but just in a “I’m busy and I’ll call you back” type thing.

Depending how she reacts will tell you if she wants to be your girlfriend or if she still thinks of you as a “brother”. (“Brother” means that she’s waiting for her ex-boyfriend to start dating her, usually!)

Don’t be confused, a lot of guys get caught in the middle of women (of all ages) play with their (ex-)boyfriends and get burned in the process.

You make her chase you a little bit, not talking for all hours on the phone, walk-by hellos in the hall at school… just play loose and don’t hang on everything she does.

If she is ready to date you, she’ll get real angry that you’re ditching her… if she doesn’t, well you never had a chance and she was just killing time with you until her ex-boyfriend came back to her.
Best wishes,

How To Seal The Deal

Dear Rob,
You seem to have a good grasp on this subject PLEASE HELP!! here we go…

I am a 21 year old college student… there was a beautiful girl in my class that I just had to get to know… so I strategically became her lab partner (4 months ago)

When I met her she had a boyfriend of 4 years whom she was with throughout all of high school… but they were on they had been verge of a breakup for a while due to his controlling nature and the fact that he hid an addiction to marijuana from her. she is a relatively strict Christian and he was not so much….obviously.

I have been very laid back with her no pressure no heavy flirting… now we stay up countless hours studying and working on homework at either her house or mine… we usually end up doing other things like going for walks, playing games, even going in her hot tub or just talking and goofing around…

Lately the past couple weeks we’ve gone to the drive in… we get lunch… she comes over on sat night and we “hang out”… she always says she’s over her bf and moved on yet she talks about him occasionally

We have a very good connection… and seem to enjoy each others company… she Emailed me a picture of the two of us… with smiley face… just little things like that… but she has never outright hinted towards liking me and it seems very casual

I’m not cocky.. but I’m not a bad looking guy, I’m athletic, I have a good job, a nice car, a motorcycle, I am a Christian like her, she likes soccer, I coach kids soccer, I volunteer for the homeless, she tells me I’m very intelligent and funny… theoretically I have a good chance?

I know giving in and telling her I feel for her is probably the worst idea… hence I have resisted and kept it casual… but we talk everyday and always know what each other are doing and always have plans with each other and we’ve gotten so close…. Rob this has gone on long enough… I have never felt like this before… she makes me weak like a little school girl and she is the most amazing person I have ever met… I have gotten this far without blowing it… but am loosing strength and I fear becoming to obvious… what can I do to make her want to be mine, WHAT SHOULD I DO TO SEAL THE DEAL?

You’ve been spending a lot of time with her and that’s great.

What you aren’t doing is being specific with her.

The next time you’re alone with her say to her “I really like you a lot and I want to make our being together official. Will you be my girlfriend?”

Just like that.

She may say “No” and if she does, then just back off for awhile.

Who knows what contact she has with her ex, maybe she needs to just to be hanging around with someone without the pressure of a relationship.

But you have to let her know that you’re falling for her otherwise the time she spends with you will simply be “relationship healing time” and she’ll start looking for someone else right under your nose.

I have a feeling that she will either say yes or she will want to think about it.
Either answer is in your favor.

But if she can’t give you an answer you’ll need to make her miss you by not being available all the time for her.

Once she starts missing you she will be more apt to decide to date you to not lose what she had with you.

Often women don’t see the best suitor in front of them until they’re gone.

To sum up:
1 Ask her to be your girlfriend
2 If she says yes, move forward
3 If she says no or she wants to think it over, become scarce, don’t hang out with her so much, give her a chance to miss you
4 Know that the future is yours, but you have to pro-actively move the relationship from where it is now to where it belongs, whether getting closer or more apart and you can start dating other women.
Best wishes,