Archive for November, 2007.

Mixing Business with Pleasure

Hi Date Guy,

Im a 37 year old female in a high powered job. I also have company that I just started. I was introduced to a mortgage broker 5 months ago by an older acquaintance. From the start I wanted to be just friends with him coz some things i didnt like: he was physically aggressive by our second date and this continued and it had the effect of turning me off – we havent slept together. Also he just didnt strike me as someone who really cared about me. He’s let slip that im a bit overweight and on another occasion said i was boring. He has been abrasive and impatient with me on occasion.

Now the housing market has bust and he’s looking for ways to make money, he has asked if there is anything he can do to help out my company. silly me, i had been prattling to him about it. Interspersed with that are comments about us having children and shared values, as well as comments about how im more accomplished than he is. The thing is I have a history of one bad relationship where i was taken advantage of and a history of child abuse. The last thing I need is another bad situation. I do like this guy and eventually told him about the abuse, but because of how he behaved before i told him i dont feel comfortable with him anymore. Now he wants to be involved with me financially. Im confused as to what to do next.

Thank you,

Dear Fados,

Even if you think the rest of my advice is crap, heed this: Do not, I repeat, do not get financially involved with this loser. I’ve had girls purposely leave behind items over at my place to insure that they could stay in touch with me after I slept with them. This would work in some regards as it would then take me a couple of weeks to completely phase them out. This would be doing the same thing, just with money. You get involved with this guy financially and it could take you years until he’s out of your life.

Everything you have written about this guy spell L.O.S.E.R. He’s aggressive, abrasive, impatient, you don’t feel like he cares about you, and he’s called you fat and boring. Yeah, yeah, I can hear you saying that deep down inside he’s a nice guy. Don’t defend him as his actions speak volumes about his true nature. He treats you like crap on a personal level, do you really think he’d respect a monetary relationship with you?

So the big question is how do you let this guy know that you aren’t going to extend your relationship? You need to use the same intelligence and ambition you have obviously used to become a successful business women and entrepreneur. Think of this purely as a business decision. Would you hire an employee who wasn’t a good fit for you company? Would you invest in a product that was not profitable? Of course not. You need to be strong and straightforward with this guy. Simply tell him that you have found it best to not mixed business with friendship. There you go, that kills two birds with one stone. That single statement lets him know that you don’t want to get involved with him financially AND that you are not interested in a romantic relationship. Don’t be surprised if he stops coming around once he knows that he won’t be getting any action or money from you.

Stand stong and think with your head, not your heart,

-Date Guy

Posted by admin in Breaking Up

Not Too Outgoing and Not Too Well Endowed

Hey Date Guy,

So here’s the situation I’ve liked this guy for a while now, met him at a societies’ freshers recruiting event (we are both at University), got his number a few weeks later, invited him round for a dinner party shortly after that, slept with him a week later. Since we slept together, he’s taken me out to lunch a few times but nothing else has happened. I mean not even kissing/touching…which i can’t totally blame him for because i haven’t tried.

I have no idea what’s going on or what to do from here.

Would appreciate any advice you can offer me.

PS: He is quite shy and younger than I am. He is also not very well endowed as far as his manhood is concern,and I am aware that he is conscious of that


Dear Nikki,

It sounds like you’ve taken the initiative since day one with this guy so it is no surprise that he’s not busting a move right now. If he really is that shy, I’m guessing either you made the first move when you two sex or that there was alcohol involved. If you are interested in this guy, you will probably have to initiate the kissing/touching one more time. He might not be 100% sure that you still like him, hence he is hessitant to make the first move for fear of rejection. Make the move one more time and unless he’s a total nerd, he should get the hint.

Now I would like to move on to the other part of your delema, the fact that this guy’s package is less than impressive. And as you mention, you know he’s self conscious of his short-comings. It sounds like you want to date him so it is somewhat likely you’ll find yourself in bed with him again. Long ago I read an advice column in Playboy (and yes, I do actually read the magazine for the articles as they are suprisingly intelligent.) where a girl was in a situation similar to yours. I felt pretty embarrased for the guy so the aricle kind of stuck in my mind. Anyway, I thought the advice made sense, therefore I’ll relay it to you as expressed by Playboy.

If he’s got a small one, the last thing he’ll want is for you to take a good hard look at it. In his mind, the more you see the more self conscious he’s going to be (especially if he’s not aroused). So, next time before you rip his clothes off turn out the lights so that when his ding dong is out, it’s smallness is a bit more hidden. Second, try laying off of the oral. If you’re down there, you’re getting to know his unit pretty well and again this only brings added attention to its size. You will not need to do this forever, but in the early goings as you two are just starting to get familar with one another it’s a good game plan. As you do it more often and get more comfortable, express to him that you like everything about him physically and that he really turns you on in bed. His guard should come down and his self confidence will go up.

Take care,

Date Guy

Posted by admin in Does He Like Me?, Sex

The Hand Slap is a Major Turn-Off

So this female friend of mine was confiding in me the other day (as she does at least once a week) about how she slapped this guy’s hand away as he tried to bust some moves. Her actions made me realize that I have some simple insider information to help you better deal with guys in your relationships.

First a little history. This girl (Let’s call her Lucy)  has been dating this guy for about a month ago. Lucy normally puts out on the first or second date depending on how much alcohol she drinks. Many guys have taken advantage of her moral flexibility as they have “hit it and quit it” as Tom Leykis would say. So now Sara has found a guy she really likes, a guy with a lot of long term potential. She doesn’t want him to bail on her like so many others have, so she is not giving up the goods so quickly this time.

A month into their dating she eventually finds her way into his bed after a long night of drinking. Lucy restrains herself and doesn’t have sex with him. In fact, she’s been telling him that she wants to take things slow and he’s been very understanding (see, he is a catch).

Fast forward to the morning and they are spooning. The guy reaches around to try to feel her up. Her response? She immediately slaps his hand away. Now all of this my seem innocent enough to you ladies, but from a guy’s perspective the hand slap is a huge, huge turn off. Here this guy is finally builds up the courage and goes in for some romance and you totally reject him by swatting his hand. What are you, his mother?

After that incident Lucy said the guy was a little quiet the rest of the morning. This worried her and this is why she was seeking my opinion. The ever familiar, “do you think he still likes me, he was acting weird” question was asked. Well, the reason the guy started acting weird is that you slapped his hand away!

It’s simple ladies, next time a guy is making an advance you don’t want or are uncomfortable with (and I’m talking about a guy you are dating, not some random guy at the bar), just gently grab his hand and tell him “let’s take it slow.” It may be your natural instinct or reflex to slap at him, but really you should refrain if you want to keep the guy around for a while. He won’t feel as rejected and will have more respect for you if you simple communicate in a nicer manner. Let me know how it works out for you girls.

-Date Guy

Does He Like Me or Not?

Hi Date Guy,

My dilemma is this. This male friend of mine has ALWAYS acted like he had something for me without flirting. When we met, I was taken and so was, and STILL is, he. When I recently broke up with my boyfriend, I told him and he seemed REALLY excited. I thought he and his girlfriend would break up because they were already having problems. I told him I liked him, totally by accident, and he did NOTHING!!

I know he likes me, and even his male assistant, who REALLY knows him, told me that as a man, the way that he’s looked at me in the office, is not a look of lust, but real “like” for a woman. I’ve ALWAYS seen this look from him, but can’t understand why he won’t ask me out now that I’m available. When again it came out that I liked him, he said he didn’t believe it before because he thought it was just “rebound talk”. It’s not, as I DO NOT go from guy to guy, and things had been done with my boyfriend for years BEFORE we broke up. Does he or does he not like me? Were the signals (a look says it all) read wrong by me, his assistant AND an intern that saw EVERYTHING and was jealous of how he treated me? Please help!


Dear Sandra,

Sounds like you might be trying to make more out of this than there really is. Does he outwardly flirt with you? No. Has HE told you that he likes you? No. Did he ask you out after you told him you liked him? No. That’s three strikes, you’re out. If this was a case in a court of law it would be dismissed. Bluntly there is no hard evidence here, it’s all circumstantial. All you have is your interpretation of what it means when he looks at you.

Don’t get me wrong, it sounds like he is physically attracted to you. It’s quite normal for a guy in a relationship to look at another girl in this way (especially if he works with her) even if he is relatively happy in his current relationship. There is something exciting about having a mutual attraction but never having to cheat in order to experience that excitement. Who knows, he may even fantasize about you. But is he ready to end his relationship for you? Doesn’t sound like it. Let’s face it, when you broke up with your boyfriend and he really wanted to be with you, don’t you think he’d make his intentions a bit more obvious? Wouldn’t he fear that if he didn’t say something that you might eventually start dating someone else?

So I think I answered your question about whether or not he likes you. Let me offer you some bonus advice about what you should do. Now that you are out of a relationship its time to focus on yourself, not him. Do some of those things that you weren’t able to do when you were in your old relationship. Live it up for a while, there is no need to rush right into another relationship. And would you really want him to break up with his girlfriend because of you? Wouldn’t you want him to break up with her because he simply doesn’t want to be with her, regardless of who might be waiting for him. Give it some time, if he really is serious about you it will become more clear down the road. Meanwhile, you’ll have to assume he’ll stay in his relationship and there is nothing more you can or shoud do about it.

-The Date Guy

Posted by admin in Does He Like Me?

Advice Given to Guys for Dumping a Girl

Just thought you girls might want to hear what some men’s magazines recommend when it comes time for a guy to break up with a girl. Here are some conflicting views from from and Maxim Magazine. One view is a bit kinder and more respectful approach than the other. I’m sure you’ll have no problem figuring out which one it is. Which one would you prefer if you were getting dumped? Personally, I recommend a combination of the two.

We’ll start with

  1. Make her the first to know. Out of respect for her, never tell your friends you’re going to break up before telling her it’s over. It’s a simple thing women consider sacred. (I don’t agree. Friends are great confidants and might be able to offer you advice or give you the support you need to go through with it. I don’t understand how this would be disrespectful to the girl.)
  2. Find a neutral zone. It’s not fair to end the relationship at your place, nor should you be forced to see a picture of you and her hugging on her fridge. (I disagree here as well. If it an emotional break up, she’ll feel even worse if she breaks down in public. Better to leave the tears at home where she is more comfortable. And definitely don’t do it at your place, you could have a hell of a time getting her to leave.)
  3. End it in person. If you’ve lost that loving feeling, be courteous and tell her face-to-face. (I agree. Email, phone, and text message may be ok…if you’re 11 years old.)
  4. Keep it simple. There’s no need to put her through the history of your decision to break up. She does deserve an explanation, but save her the long-winded reasons of exactly why and how things went sour. (Agreed. The longer you talk the more ammo she’ll have to get you to change your mind.)
  5. Get her to see your point of view. You’re probably not the only one that’s been feeling the relationship going downhill. A dose of reality might be just what the doctor ordered to get her to accept what it is you need to say — and do — about it. A good way to get her to understand why you and she aren’t best suited for one another is through a simple example. (No, no, no. For example, what if one of the reasons you want to break up with her is because she is lousy in bed? How could telling her this be of benfit to either of you?)
  6. Don’t change your mind. There’s a big reason why you made the decision to confront her with the end of your relationship, be sure and stick to your guns even if she cries. Remember, you wanted to stop dating her for a reason. (Agreed, 100%)
  7. Be ready for tears. Whether she’s glad you said something or not, chances are tears will be shed. Ending a relationship can bring intense emotion and she’s not about to save you from seeing it all pour out at once. When she does start to cry, be sympathetic but don’t be drawn in by an overflow of powerful emotion. Be an emotional rock. (Maybe. I’m on the fence with this one. If you throw a couple of tears in there yourself, she may let you off the hook a little easier.)
  8. Have an exit strategy. Make sure to have plans set with friends later that day. This will ensure that the breakup process isn’t dragged on longer than necessary and that you’re not alone if you feel bad about what just happened. (Agreed. I would suggest making plans with family, not friends. Ditching her so you can hang with your buds may be a bit callous in her view. However, if you have to meet up with mom and dad for dinner at a certain time it will be more difficult for her to be upset with you for cutting out.)

And what does an article from Maxim Magazine recommend? Read the rest of this entry »

The Art of the Subtle Pick-Up

Some girls are clueless when it comes to pick-up lines, especially if they are subtle and don’t appear to be your normal cheesy line. This point was illustrated this afternoon as a guy struck up “harmless” small talk with my girlfriend at Starbucks. Here is how it went down. As she’s walking out of the place this guy comes up beside her and comments on the odd group of loud bikers that had congregated outside of the mega coffee house. He says something along the lines of, “Did you see that group? what’s that all about?” It’s an open-ended and non threatening question. Because she found the group odd as well, she responds something along the lines of, “I’m not sure what was going on, it’s kind of weird.” And there you go, the wheels were set in motion and a conversation followed and he eventually asked her out. When she told me about the exchange I mentioned it was a good pick-up tactic on his part. She seemed bewildered by my comment and responded that “he was just being friendly.” The fact that she seemed so oblivious to this sort of pick-up technique really surprised me and got me thinking that it would be a good subject for me to write about.

The exchange with the guy from the coffee house didn’t bother me one bit. First of all, I trust my girlfriend 100%. Second, I view it as a compliment when a guy finds her attractive enough to approach her in hopes of securing a date. It makes me even more proud to be with her and reminds me of how lucky I am to be with her.

So how do I know that this was a pick-up attempt? Well, I used that technique all the time back in the day and was quite successful at it. Striking up a conversation with a girl who you don’t know is very hard if you ask her a question relation directly to her. For example, if a guy approaches you and asks you how you are doing or tells you that you are pretty, it’s easy for you to see that he is interested in you which will (if you are not overly attracted to him) cause you to go into a defensive mode. On the other hand, if you approach a girl and make a comment that has to do with someone or something else (especially if that someone/something else was out of the norm), you establish more of a common ground and takes the pressure off of her.

Case in point. While in college, I found it very easy to meet and date girls who I shared classes with. My strategy was to simply wait until the teacher or one of the other students did something that was very odd. You know, the guy in the front of the class who raises his hand every three seconds and asks one bizarre question after another. Class is dismissed and I simply say to my target, “What’s up with that guy and all of his crazy questions?” Inevitable she’d respond something to the effect, “I know, he is totally weird.” Ah ha! The ice was broken and a we begin a conversation about something we both found interesting.  From there I could later transition into asking her about herself and roll that into asking her out. It gave me a chance to interact with her and make her feel comfortable with me before I showed interest in her. This tactic of mine was applied in many different situations (at a store, a bar, wherever) and increased my odds of getting a date considerably.

So next time a guy chats you up for what you think is innocent small talk, you might want to see it for what it might really be, an attempt to pick you up. Now this isn’t necessarily a bad thing, especially if you find the guy attractive. However, if you don’t, you may want to get out of conversation sooner rather than later.