Tag Archives: Dating Advice

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.


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,

She Told Me To Call Her, What Does That Mean?

Hey Rob,
I ran into an friend I had in math class with (at a community college), we talked and she was happy to see me. As I left I told her to call me sometime, but she replied with, you have my cell phone, remember?

Is this a good sign? Does she sound like she wants me to call her?

Hi Sidney,
Yes, it’s a good sign.
Call her tomorrow and make plans to ‘catch up more’ the next afternoon. A nice friendly place for a coffee or lunch, be sure to split the bill or go ‘dutch’. (When you sit down and get the menus just say “We’ll split the bill, OK?”)

Guys have to keep in mind that women want to be fought over. Leaving a call up to them is the same as saying to her “You’re interesting to me but unless you make all the moves nothing is going to happen”. And usually that is what happens… nothing. Because the guy just proved he’s a wuss.

Then the guy wonders why she doesn’t call…
“She seemed so interested when we talked that one time…
Blah blah blah.”

Guy’s may play games to try to spark her interest, but girls are much more forthcoming and honest, so that the guy has to make the moves, take the initiative and instinctively prove themselves to her that they are worthy of her.

This isn’t a guy’s wussy “I like you, I love you, I beg you to like me, to love me too” type situation. It’s taking the bull by the horns and making a commitment to the next stage of your emerging relationship.
Never let it pass when she says “You have my number, right?”.
Make a plan to call her and have a plan ready for when you get together, within a couple of days.

Never, ever, tell a girl that you’re interested in seeing more of to “Call me sometime”. It’s a deal breaker.
Best wishes,

Guy’s Ignore Game Times Three

Dear Rob,
There are three men of interest.
Guy #1, is a workmate who I sporadically interact with due to work. He used to draw attention to himself by talking loudly or being animated. We would talk mainly about work related stuff and sometimes joke around. He now, ignores me to such an extreme. He pretends he doesn’t see me though our paths cross.

Guy #2, is a friend who has admitted to others that he finds me attractive. He has dated two of my friends in the past who he has also told that he had liked me. He and I are friends that hang out on occasion and just have a good time. It has never progressed to anything more…for two reasons, I don’t feel an attraction for him and he’s dated two of my friends. He, also, has gone out of his way to ignore me to the point of being rude. He has never actually asked me out; thus, I never had to turn him down. When he’s in a bad mood he’ll ignore me even after I greet him and we make eye contact.

Guy#3, He has hinted at having an attraction for me and has hinted at going to dinner; however, never quite asking. He was doing an athletic event and asked if I could come along to help out. I, of course, agreed. After the event, he kissed me and asked if I wanted to go to dinner. After dinner we parted with another kiss. We met up in the evening again for part two of the event, another kiss. The next couple of days were very nice with lots of compliments and attention. Then one day, it stopped. Now, he is acting very odd, as though I make him uncomfortable. He ignores me even when it is obvious he sees me but we train together twice a week and on these days he is flirts with me and puts his hands around my waist.

Sorry for it being so long….what I want to know is what is with the ignoring? Is it something I am doing?

Hi Martha,
I’m going to start my reply by assuming a couple of things:
I think you’re a great looking girl, probably a 9 or a 10 in the looks department.
I bet you don’t have many successful dates because you don’t put up with insincerity, immaturity and general childishness in guys.
You are turned off by the wussy-type guy that tries too hard to please you, tries too hard to be funny…. the idiotic things that some guys to to get a girl’s interest.
I also bet that you wait for the guy to make the first move on you, asking for dates, suggesting things to do, etc., and half the time you’re too busy with other things to accept the date ideas or take them to heart. You unintentionally shoot the guy own.

If you have the power to intimidate guys, through your good looks or bright attitude, they will pull shy after feeling shot down and start playing the ignore game after just the briefest of encounters.
These wimpy guys are centered on ownership. They want to control and own you and when you can show them that you are your own person they run scared because they don’t know how to deal with a successful, good looking, assertive woman.
They are children dating in an MTV world, not able to work through their feelings or interactions in real life when what they do doesn’t resemble a stupid TV show. These guys haven’t learned the slightest clues about dating and being a man around a woman.

Now then:
Guy #1
This is a guy that practices comedy to attract women and closes up shop when he doesn’t get the responses he wants. He’s a fool. He wants to control but will not break out of the mold of self-importance to accept the fact that other people have thoughts and feelings too, that others sometimes don’t think of him being so important. This is why he now ignores you.
The next time he walks by you say to him “You were funnier when you could talk to me”. And let him fumble his response.
Likely he’ll think of you a bitch, but at least then he’s making a stand for his feelings of you. And you’ll get some closure from this jerk.

Guy #2
He has dated your friends only to get closer to you and try to date you. Now he knows that you’re in a league far above him and he’s playing the hurt puppy knowing that he’ll never have you.
I’d point-blank ask him if he knows of any single guys that might want to date you. His response will confirm what I’ve told you.

Guy #3
He’s too scared to fail with you, so he’s decided not to get his feelings hurt by your possible rejection. Likely you’ve confided in him about the other losers you’ve dated and he saw himself in what you said.

He may be a wuss that doesn’t know how to communicate with women other than trying to buy their friendship and acceptance. This type of guy is deep into the “ownership of commitment” and I’d steer clear of him no matter what. Until he realizes that men and women like the same things, have the same needs and goals in life, he’ll always think that he comes first to the point of trying to control everyone else’s actions in his circle of friends.
I’ll bet that any relationship he’s had in the past ended badly because of his insecure needs and controlling attitudes.

You can verify this by doing a little research and talking to any of his exgirlfriends.
The next time that he flirts with you and puts his hands on your waist, put your hands on his. Pull his hands away and tell him that touching is not permitted.
One of two things will happen next:
He won’t blush or apologize, he’ll get upset is my bet. If he does that he wants to own you and he’ll start by making you apologize for his familiarity in touching you.
If he does blush and apologize, he’s just a scared little boy that doesn’t know how to get past the first date and if you’ve managed to talk to any exgirlfriends I bet that you’ll find out that he moved too fast, held on too tightly and broke up very badly.

He maybe a “clinger” that just wants romance that he can manipulate on his terms only.
Best wishes,

Please Help Me With The Girl I Like

Dear Rob,
I’ve been looking aimlessly for help and recently I stumbled upon your site and I really like the advice you give so I was hoping to come to you in seek of personal advice.

You see me and this girl both in high school (both 16) go to the same school but never talked to each or had any contact ever.

About a month ago I found out form a friend that she thought I was really cute and when my friend told her that I’d be interested she was beyond overwhelmed.

The thing that got me the most is that she is by far the most beautiful girl in our grade of and perhaps the most prettiest in the school. She is really popular and she mostly hangs out with older kids.

However myself, well I’m just an average person nothing special or popular or anything like that and for someone like her to notice me is just absurd.

But anyways, my friend gave her my number, screen name and all that and told her I’d contact her which I did and we started to talk casually and it was really great.

She talked to my friend and told her friend that she was thinking of going out with me which confused me because we only talked for about a week but I still continued on.

Things were absolutely perfect and we were planning on seeing each other since we never even spoke one word in person to each other. The first time we made contact was the day after we first talked when I said a casual hello and she waved with a large smile. We then talked again online and we agreed to hangout sometime during the break which was soon approaching.

As we talked for the two weeks before break she began to stop talking in middle of our conversation.

I found it out from her friend that she loves to play hard to get and does this to every guy. I figured I’d have to play back only I did not know how so my friends gave me advice.

Well she was beginning to be cold and things looked confusing until I asked her to hangout and she did not answer. Then late that night she texted me with smiley faces and exclamation point saying hey, however I did not reply.

I instead talked to her the next day and never spoke of what happened that night. We then talked again about hanging out before the breeak and when I asked she did not reply again. I waited for 20 minutes and then said well I guess you don’t want to be bothered. She quickly replied saying I’m sorry I didn’t see your instant message but I’d love to hangout.

So we set a day for the break and I was beyond excited.

As the day approached I tried to contact her but it was to no avail. Instead I contacted her friend who was also joining us along with my friend so we could all be comfortable.

Her friend said that she couldn’t anymore because she wasn’t going to be around. I was baffled because we made the plans one week in advance and she never even bothered to tell me that she couldn’t hang out anymore.

I decided to not talk to her and just forget about it until she contacted me two days after apologizing and saying that she would be free to do something the next day if I was still willing. Of course I said ok and things were perfect until this time her friend couldn’t come because she had practice for her team. She told me it was ok and that we would find another time.

Later that night my friends tried to surprise me by taking me out to see her so I called her to see what she was doing and she said that she was with another one of her friends and that she would call me back as soon as she got ready.

So my friends and I drove around waiting until we called her friend who said that she must have fell asleep because she was tired and went home.

I later found out this was a lie and that she really went to some other kid’s house. The next day her friend said that she talked to her and she said to her that “I text her almost everyday and she isn’t that type of girl who likes to be bothered all the time”.

I really was confused because just two weeks earlier she was going crazy for me and all into me and she always thought I was cute and wanted to hangout with me even saying she was thinking of starting a relationship with me.

Now all of a sudden she just changed? How? Why?

I am so confused because I was so sweet to her and although I did text/instant message her almost everyday we still were fine.

School has started once again and since that day we haven’t talked, its been about two weeks now I just don’t know what to do.

It is vey hard for me to move on and I really am open to anything to get her back, I just don’t want to waste this chance I had at an amazing girl please help me!

How could I mess up such a big opportunity when I was so nice and sweet to her.

What could I have possibly done wrong and can I turn it all around?

I’m very sorry that this is long, I just need help hopefully you can do that for me. thank-you for your time..
– Lost Without a Clue

Hi Lost without a clue,
I feel your pain but what you are experiencing is a normal part of growing up.

Boy likes girl,
boy talks with girl,
girl suddenly ignores boy,
boy can’t figure out what went wrong and gets depressed.

The main problem is that guys and girls, under 21, maybe even older, have a real lack of communication skills.

It’s easy to chat online, send smileys and all that, but nothing important and interesting is ever said. There is no real communication because you haven’t been taught what to say.
And when face-to-face time is available, both guy and girl don’t know what to say, what the next step is, so they play shy and rely on the other to say something like “Let’s hang out” which is a basic promise that isn’t followed up because it starts the whole “Dating thing” cycle, which can lead to a breakup, which also leads to heartache and who wants to go there?

So, the guy likes the girl, the girl likes the guy and the relationship is stalemated because no one wants to take the next step and have to worry about rejection and breakup. Or what friends might say and all kinds of nervous things like that.

If you’ve been able to follow along, this means that you didn’t mess up, you haven’t lost a great opportunity because it never really existed!

You were being played but not in a bad way, this just happened because there are no rules to follow for young people to just “hang out” and try to “date each other” and understand what is going on.

So, because these are unwritten rules, they are instinctive, not verbal, I will give it my best shot to provide a guideline that will get her back for you.

1. Communication

If you have something positive to say, then say it. Don’t chat online by sending smileys, that really isn’t communicating, is it? If you have to IM her, tell her what you’re doing right now, tell her what you have planned tomorrow and ask her to meet up with you, then end the IM.

Sending smileys and silly IM notes is really just an empty, awkward pause in a conversation and get’s boring really fast, so just don’t do it.

The main reason teens don’t date is because they don’t know what to say, although they know what type of response they’d like.

Heartache and heartbreak is very real at this age (well, really at any age) but the nervousness of being ignored or rejected can be overcome by communicating with the girl you like.

2. Hanging out

One of the hardest part of liking a beautiful, popular girl (and even the shy ones for the most part) is planning a time to spend together, to hang out, where there won’t be any awkwardness.

To avoid this awkwardness you nee to “have a plan” that when you meet up with her, you have something to do with her. And I’m not talking about anything sexual, just something to do together, like window shopping, talking about vacations, places you’d like top see, the career you want to do, not too heavy but fun, interesting talks together. Walk in a local park, go to a local museum, head to the library and check out some books… get the point? Hanging out with her doesn’t need to cost any money but it must involve the two of you, of the two of you and some friends, actually doing something.

3. Sharing each other’s company

You like her, she likes you, and you know this because of you asking her friends whether she likes you and so this game begins. But, and this is a biggie, if you act on the info from her friends at this point you must, directly, ask her to hang out with you at a certain time, a certain place.

If you both are too shy to plan actual time together, whether alone or with friends, too shy to talk about things without awkward pauses, then you need to remember, you are sharing time together.

It’s very likely you are sharing the same feelings for each other too, but cannot overcome time, space, and the mass confusion of life that surrounds you to easily overcome this awkward pause of life and get together.

So you need to say to her (NOT I like you) I want to hang out with you at “this place” on “this time”.

Have a plan to share time together, make the effort, don’t just roll along like a tumbleweed, waiting for someone else make the magic happen between the two of you.

4. Understanding the very real chance that getting together might involve breaking up at some point too

Hanging out, spending time together, is all very good and real. But, at a young age it’s easy to make future plans with the one you like that aren’t really going to happen. You are always on the verge of the awkwardness happening and a break in sharing, a break in communication, then it happens, she doesn’t like you any more and you find yourself in a break-up. Getting together, spending time together, is great. But don’t plan for the long away future with her because then she knows that you’re really just a wussy and she can control you and she wants a guy that’s great too and she ends things with you because you want her more than she wants you and you’re just dragging her down and you talk about nothing and when you say you love her it’s just because she’s popular or great looking but doesn’t involve the real, inner her, and she senses this and dumps you.

Out of these 4 sections we can boil everything down to:

Don’t be a wussy;

Talk with her and when the talking is done, well stop talking. End the IM, hang up the phone, stop texting her, etc;

Have a plan;

Share time at first, share feelings after the real connection is made;

Be nice toward her but be calm and cool too, understand that women like guys that seem to have everything under control, not nerds or jerks.

There are a lot of places to find more info like this and I suggest: www.doubleyourdating.com

This will give you a heads up, even if you don’t buy the ebook but just read the weekly newsletters.

So, now you know what to do and handle this situation with the girl you like.
Best wishes,