Category Archives: Dating Advice

Dating advice for singles of all ages

Where is this relationship going?

Hi Rob,
I came across your website and I thought it wouldn’t be a terrible idea to email you to ask for relationship type advice.

I met a guy about 5 or so years ago. When we met — it was an instant atttraction—we both knew it. We discovered we had several commonalities— different ethnicities, common interests. We spent a fare amount of time talking and getting to know each other. We exchanged contact information and said we’d keep in touch. The last day of the week away at the same place, before we all left, we kissed…

We kept in though mostly through email throughout college, until this guy finally got a cell phone. Emails were always great and was always good to hear from him. Two years after we met… he called me to say he was going to be in the area and that he would love to come for a visit. Fully knowing what to except, we hung out over the weekend and slept together. I had a great time with or without the extra perks of the weekend.

After that weekend, we went back to our normal lives, we talked on the phone every so often, email and instant messaging.

We eventually became Facebook friends, if that means anything or not. Due to crazy schedule— me being and school and this guy working a good bit, we didn’t hang out again until the beginning of the year when he came to visit me—a 4 1/2 hour drive for a long weekend. We had a great time catching up, talking, watching movies, going out to dinner and again sleeping together.

We continued to stay in touch after that weekend… texting, touching base over the phone sometimes and Facebook.

The following year he came to visit again, and flew from his hometown to visit for the weekend. We had another great weekend of catching up, chilling, hanging out and some fun.

Since then, we still connect via phone and all the other social networks. He’ll text me a “Happy Birthday” on my birthday and I do the same on his b-day.

I feel that we connect on different levels with or without the extra perks.

I just want to know where this is going if anywhere and if I should keep this going.
Let me know your thoughts.

Much Appreciated,
Unsure of what to do

Hi Unsure,I think that if it was to go somewhere you wouldn’t have to ask me.

So it’s time to ask him. Straight out, on the phone “Is this going somewhere?”

You know what my answer is, what’s his?

Best wishes,

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!

Be The Master of Attraction

Being the “Master of Attraction” (or Mistress of Attraction”) is something that we all strive for, at one time or another.

Seeing for the first time that cute girl or hunky guy always brings our insecurities to the surface, what do we say, how to act, talk, stand, sit, etc.

When you believe that everything you do affects everything that happens to you, you are on the road to being a Master of Attraction.

Understanding that even the insignificant things you do can have a “butterfly effect” on others should help you to strive for pleasantness in all that you do But the doing is always up to you.

So take this thought with you: you are always being watched, being judged, but you will always be remembered for the things you do.

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!


He Doesn’t Know I Love Him

Dear Rob,

I have a long term friend. We fancied each other, said we had feelings, but nothing ever came of it. I am insecure & he is a flirt, so we had lots of fights & the friendship has taken time to come back.

The other night we are at a work do. We barely say hello or look at each other, he is with lots of women, one in particular who adores him is all over him. We exchange a few words at the end of the night, she drags him out to dance, gets a bit heavy. So I go to get a taxi. Minutes later he is outside & says he is getting a taxi, then walks off.

Next day he comes up to me, we talk about the night, he stands very close, seems emotional, then we are interrupted by another friend and he gets annoyed at the interupt. He keeps coming back over & is all friendly and nervous bt I dunno if he felt sorry for me or if it was interest.

He is equally attentive & gentle later on, which he hasnt been for over a year.

Next day, he flirts with her again while I am sitting nearby. Today, as I am talking to him, she passes & he is all friendly to her. I walk off & when I meet him again he looks at me and smiles but when I drop my head he goes cold again. Today he was less affectionate.Yesterday it was like he was almost panicking.

I don’t know what to do. I love him still. I can’t be his friend & be OK about him being with other women. Does he have any clue how I feel do you think? And why the nice one day, back to friends the next?

He was so close to me the day after the night out that the guy who interupted thought it was suspicious and actually stood next to me even though he was not welcome.

Is this guy actually so cruel (I find it hard to believe cause he is a nice guy in general) that he would just not care how I feel? Does he not know how I feel? Or is he trying to provoke me into some kind of action?

Bear in mind all this is going on and we barely speak to one another. We are just work colleagues with a history of what was once a deep friendship.We have never slept together. I know that he genuinely cared for me in the past. I will not show emotion though or give him attention & this was what drove us apart in the beginning. He tends to go for women who show obvious like for him.

Please help me Rob.


Guy’s don’t know what isn’t told to them.

He’s a flirt because he thrives on attention and he puts in it your face to say “that if you’re not interested then so what, there’s other girls”.

I see a lot of conflict if the two of you were to start dating because of the conflict of personalities. You look for comfort and he looks for approval, not a good mix.

You say you love him but all this is unstated?
You are in a fantasy that has to end, here and now. Unless you can live with picking up his dirty socks every night.
Good luck!