Category Archives: Dating Advice

Dating advice for singles of all ages

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.


Has She Lost Interest?

Dear Rob,
I’ve been enjoying your advice and think you have some great opinions
to offer so here goes.

A girl started a 7-week internship at my company recently and we hit it off right away. After a couple days of work together, I gave her my phone #, which she thankfully accepted. She didn’t give me hers in return claiming she doesn’t “give her number out to very many people” to which I replied with a shrug and a laugh and said “we’ll see.”

That same week, I invited her to play some tennis after work; she said yes and we ran around for an hour chasing tennis balls, having a great time, and flirting the whole time.

The next week the subject of favorite foods came up. I found out hers is Thai, as is mine, and so I asked her if she wanted to go eat some Thai food. She responded “I’m trying to save money right now,” (she is paying for college credits to work somewhere for free-I still don’t understand how they get away with that-and gearing up for a European vacation) and so of course I offered to buy. She said she didn’t want to do that because she’d feel like “she was taking advantage of me,” and so instead of pushing it I just said OK. That same night, she text messaged me (giving me her phone #) wishing me a great weekend because I was leaving for the weekend the next day, and also saying she thought we should go out for Thai after all.

We went out the next week, had an amazing dinner, found out we have the same or similar values, passions, and center, so to speak, in our lives and it was great. She made it a point, though, to tell me that “this isn’t like you taking me out, you’re not paying for me, I’m here because I want to be here.” I guess you could say she threw me a major curve ball.

Here’s where it gets interesting. The next week, she invited me to ride with her to the town her college is in. She had to go up for an evening to help plan some events for her upcoming graduation. It’s about an hour away from where we work. I have friends up there and she knew this, and so her thought was we could ride up together and while she did her school thing, I could hang out with friends and then we could ride back home together. We had a great ride up, had time for pizza in the park, and then after she was done, she came over and met some of my friends before we left. It was a good night.

The next night, we went to a football game together, got take-out, went back to my house, watched a movie, and flirted the whole time. It was a good night. Other than halfway laying on each other and that sort of thing, it never got physical. Also, the subject of our relationship never came up and I never made a point to bring it up. I thought it was becoming pretty obvious we both liked each other. And, since we work together, I’ve been hesitant to move too fast. I didn’t see her the rest of the weekend because I was at a bachelor party (no strippers or anything like that, just guns, meat, beer, and competition-that sort of bachelor party).

This last week was her 6th week and it was an awkward one. I felt like she was annoyed with me all of the sudden. Where before she would pass by and smile, it was like she was ignoring/avoiding me, going out of her way to not walk past me. We had a dinner and movie at my place scheduled for Wednesday. On the day of, she insisted on inviting another girl we work with to come over too. The girl is here from overseas and doesn’t know anyone and so I’m all about having her over, but all I got from it was “I don’t want to be alone with you.”

I asked her if we could do coffee and talk this morning (we both have the day off from our job together but she works another job in the afternoon). I figure it’s time to be completely honest with her and see where she’s at. She said she was still in bed and wasn’t up to it before work but “if you have something you want to talk about, we’ll find a time.” What should I do? Should I wait and talk after this next week, her last week at my company, is over? Why the change in attitude, especially after initiating the car trip and the dinner? Did I miss my window? I just don’t get it. Let me know what you think man, I’d appreciate your advice. Wow, this is long, sorry about that Bro.
P.S. She’s 21 and I’m 24. We both do basically the same thing.

Hi Confused,
The easy answer is that, yes, you missed your window.
She was open to your advances and you didn’t advance far enough.
From what you told me she was playing it slowly, making sure you weren’t a player and her attitude became more serious with you when she took the ride with you to her college, you both did your own things, and shared the ride home again.

After that you should have turned on the heat and gotten serious with her. Now, she may be past what she felt for you, figuring in her head that she imagined everything and you’re not that serious after all.

How to become serious after her starting to lose interest?
That’s a tough question.
The answer is harder.

In your current situation I don’t think that you want to let her get away. Make your move on her last day with your company. Invite her to dinner, make it special. You’ve both shared time together, now it’s time to share some romance.
Simply, this is the way to accomplish setting the scene:
Order a dozen roses to the restaurant where you make the reservations and call the restaurant to expect the delivery and have the flowers on the table before you are seated. She’ll see the roses and know what you’re feelings are, unmistakably.
This will be the “make or break” moment, but I’m sure you’ll pull through, no matter her response.
Best wishes,

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,

College Freshman Dating A Highschool Senior? Not Likely!

Dear Rob,
I recently confessed my affection to a guy friend of mine and to my surprise, he felt the same.

We sat and talked, discussing if we wanted to become more than friends. He suggested that we go on a date, to see where we could take things. So we go out and things are going great. When people ask him if I was his girlfriend he tells them I am. But we get back to his car, we start to discuss our relationship in detail and he reveals to me that he is unsure about us because while I’ll be starting my senior year in high school, he’ll be starting college at a school an hour and a half away from me.

I started to become frustrated with him because he keeps telling me that he really likes me (even mentioning examples) but how he is somewhat swayed by “outside forces”.
He is a very smart guy and a very logical thinker. That’s why he’s had so much trouble deciding. He begins to tear up because he “doesn’t know what to do.”

We decide to leave and head for a park to walk. So while he’s driving, I tell him that I’m sorry… that I shouldn’t have put all that on him but it’s just I have such strong feelings for him and I’ve heard the “long-distance relationship insecurity” thing before.

We both start crying and he tells me that he’s sorry too and I admit to him about my past relationships and how they never seem to work out and he tells me that any guy that wouldn’t want to go out with you is crazy. So we get to the park and talk and have an amazing time. We come home, kiss, embrace and I tell him that I want to see him before he leaves. but since that day, I haven’t received any communication from him although I see that he checked my myspace page quite frequently after our date. I told him how I felt about the whole thing but I haven’t talked to him since. I’m trying to give him his space but it’s coming down to the wire. And I really care about him but I don’t know what to do. I feel emotionally exhausted about the whole thing. 🙁

Thanks for reading. Hope to hear from you soon. 🙂
Hopeless in Colorado

Hi Hopeless,
This guy doesn’t need his space. He needs his life. And what he fears most is that he’s going to be a college freshman dating a high school girl.
Trust me, it’s not going to work. There is distance and the school bias working against this. Your guy knows this although he also knows what he’ll be missing if he doesn’t date you now.

He’s already showing you his doubts and, with distance and a new life and the college world in front of him, your relationship won’t last if you let it get started. And he’s ignoring you so that he doesn’t have to say this to your face.

Remain his friend but know that your lives are about to take different directions. Do not get involved at this point. If he asks you why you’ve decided to remain friends tell him what I told you.

And next summer, should you both be single maybe you can really become more than friends. But not before. Too many changes are going to happen to him, and you, in the coming months.
Best wishes,

Too Young To Date

Hi Rob,
I’m in love with one of my best friends. Except she has a boyfriend… but the relationship is going nowhere.
She says it herself, but she doesn’t want to break his heart. How can I make her know I love her more than anyone ever will?
Please help me. She’s the one. and I can’t lose her.

Your email tells me that you’re young.
And inexperienced as far as dating goes.
I’d stop being such a love-sick puppy about this girl and wait to date when you’re more mature.

For instance, you say that “I can’t lose her”, yet, she’s not yours.
And if she doesn’t want to break up with this other guy, but listens to you moaning about how much you like her… UGH.
Do yourself a favor, stay single, wait for the real right girl to come along, in a couple of years time.
And the next time you have a relationship problem talk to your parents about it first.
Best wishes,