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My column is dedicated to telling it like it is. I will always give you the best information available to me or the best advice I can. I will be upfront and never hide the truth from you.

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So I've been dating this boy for about two weeks. I'm 22, he's 24. We've gone on three dates and I felt like the first two weren't that great. He's kind of quiet, a little uptight, and can be awkward. Both dates we went out for dinner and then got drinks at a bar, which I'm not usually into, but it seems to make him loosen up a bit.

The third "date" I invited him out with me and my best friend to go dancing to try and see him loosen up even more. I drove an hour out to pick him up and then an hour and 40 minutes to the city he wanted to go to because he knew a bartender at one of the clubs who could get us in for free.


I danced with him a lot and tried to teach him how, but even after he was kind of drunk he was still kind of awkward about it. He wound up kissing me a few times, mad some sweet comments, and all in all we all had a good time.

I drove my best friend and him back to my place and they slept in the extra bedrooms I have because they were too drunk to drive home. Before he went to sleep he kissed me one more time, which I thought was sweet and I felt good about everything.

In the morning he was quiet, awkward again, and only said maybe three things to me. I drove him an hour back home and he didn't kiss me again or anything, he just got out of the car without even a thank you. So then I had to drive another hour back and I was kind of mad about all of it. I spent around $100 between gas, drinks, and dinners on our dates that I really could have used and I felt like they were wasted on a guy who I probably wouldn't see again...

I crossed him off my list and then a few hours later he texted me asking if I wanted to go out again. I told him how I felt and he apologized and said he was just really shy around me and that he does like me and was worried he ruined the night with his bad dancing.

I think he's cute, admire his ambition, and like how intelligent he is. I enjoyed it when he was being sweet to me and when we kissed I did feel like there was something there.

However, I'm not the kind of person who can deal with a man being awkward and constantly clamming up. I prefer men who are chatty and can take some kind of initiative because I tend to feel badly about myself if I think a guy doesn't like me and wonder what I did wrong. I also get really quiet if it seems like they don't want to talk and tend to put a wall up if they seem disinterested.

I also think this might lead to future issues if we decided to be intimate. I feel like he wouldn't know what to do and I like for the man to be the dominant one in bed. Last time I was with a guy where I had to be the dominant one I hated it and never saw him again. It was just so awkward and I don't like guys who don't know what they're doing. I know it's possible to teach somebody, but as a young woman it's hard to give a man sexual advice without them getting offended, no matter how sweetly you ask.


Anyways, should I give him another shot or should I move on? What do you guys think?



You have two issues here both of which are important. I can speak on both topics from experience as I to was the awkward guy until I met my wife.

I could talk to a girl over the phone for hours but in person I could not hold a conversation. When I met my wife she somehow realized this and slowly brought me out of my shell. I don't know if you’re in to auto racing but if you are you will recognize the Dale Earnhardt Jr. Until he met his wife Amy Dale never said much in interviews. After he met Amy and they dated awhile he started to come out of his shell. Now you can't shut the guy up. There is an old saying; "Behind every good man there is a good woman." You might be that good woman.

You are writing us because I believe you see something in him you like though you two are very much alike in that you suffer from some forms of social anxiety. This can be overcome and you can do so together alone or with professional help.

It all starts with having a conversation about feelings. He has said he likes you. You think he's cute, admire his ambition, and like how intelligent he is. It is time for you to reply to him that you like or admire him. Invite him over for dinner. Over dinner you tell him you would like to see if a relationship is possible but that the two of you are very much alike in this one way. You say you’re willing to work on it wife he is willing to do so and you can do so together. If he says yes then this guy is a keeper. Get couples counseling to help you get started on the anxiety issue.

Now for the sex question you have. Every relationship including a sexual relationship requires communication. We are born with the mechanical knowledge of how to copulate but not the finesse that current lovers want from sex. Boys learn everything they know about sex from porno movies. Not the best way to learn about sex and pleasing a partner.

When my wife and I were headed into her apartment for our second night of sex as we crossed the street from the parking lot she very calmly said, "I'm more vaginal in what I like. Our first night in bed I had spent most of our oral sex concentrating on her clit. As we continued our relationship we refined our love making with each of us telling the other our likes and dislikes.

Sex is something we learn as we do there has to be open communication between partners. My wife likes to be the dominate one on occasion. That's fine I can be the submissive and let her do her thing with me. There is nothing unmanly about it. Why is that so; simple. What happens in the privacy of one’s bedroom stays in the bedroom.

You and your partner should first be comfortable enough wand trusting of each other that you can experiment with your sax play. As long as both consent to what it is you want to try there is nothing weird about it. But it all starts with a conversation.

Conversation is the key element in any relationship be it a sexual one, a business one or just a friendship.


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(Rating: 5) Thank you! Unfortunately, it wound up not working out as he was too self conscious about it all to keep in touch with me after. His loss I guess. :/
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