Ask Amber: This dude’s lady is making him all nervous

By | April 4, 2012 at 2:20 pm | 2 comments | Ask Amber, feature slider, Features | Tags: , ,

Deedle Doodle,


This week’s question:

Hey, Amber:

Your column is insane, but it makes sense in a twisted way. I wanted to see if you could help me with this. I’m a 27 year old male and I recently started dating an older woman. She’s 38. I’m not myself around her. She’s nice and I don’t know why she makes me nervous but she does. She’s very confident and busy with her job. I feel like I’m always waiting around to see her. I usually date party girls, and have always been the dominant one. I think I’m in love with her. I don’t know, I feel crazy. So….I guess my question is, how can I relax and be myself? What do you suggest?

You Can Call Me Space Cowboy



I think I want to call you Sidesaddle Sally. Is that ok? Sure it is. I love this question, and I think it’s great you’re aware of your feelings and want to find ways to feel comfortable. Your girlfriend sounds like she has more confidence than you. That’s it. It’s unbalanced. If you two were legs on a body – she’d be the normal leg and you’d be a stump. Basically, you and your girlfriend are pirate legs.

You probably found comfort in dating party girls because manipulating them is easy. They’re always drunk or high. You could be like, “Hey bitch, make me a delicious sandwich!” She’d probably think you’re funny and make you a delicious sandwich. Or, if she’s a mean drunk, she’d punch you in the scrotum sack. The next day she’ll feel guilty for injuring your testes pouch, and will do whatever it takes to make you happy. Party girls are unpredictable in the most predictable way. Oh, and they cry a lot. Sounds like a handful, but one thing is for sure– dating this type of girl makes you believe that you’re the one in control.

If your girlfriend continues to have confidence, and you continue to have insecurities, one of these three things might happen to you:

1. You’ll turn into a cry-baby-boy who does whatever she says AND you’ll cheat on her just so you feel like a man.

2. You’ll become resentful and will attempt to compete with her, or you’ll glom onto any success she has (as if it’s yours). Your intentions will be obvious and her friends and family will say, “Instead of trying to take what she’s worked so hard for, why don’t you burn in hell forever?” Then you’ll get scared and hop on a horse and ride sidesaddle out of town.

3. You’ll become an empty shell. You’ll hang out at home all day, bored with no purpose in life. Maybe you’ll try to enhance your penis. I DON’T KNOW. WHY DON’T YOU TELL ME? I’M SICK OF HAVING ALL THE ANSWERS. That would be funny if you went to therapy and your therapist was like, “SHUT UP. ALL YOU DO IS TALK ABOUT YOUR PROBLEMS.”

Anyway, if I were you, I’d go with option number one. You’d be fake-nice to your girlfriend AND you’d get some sex pot action on the side. HOLLAH.

Maybe you feel weird around her because you’re young. This will totally offend you, and other young men, but I think most guys in their 20’s are fucking idiots. I think they should be quiet until they’re 30. Seriously, I’d be careful; it’s weird that she’s dating you in the first place. Maybe she needs to date someone insecure so she can manipulate them. Oh my god– you are the drunk girl in the relationship! Holy crap. Make her a delicious sandwich or punch her in the pussy! Let’s get this party started!!

Ok, let’s move onto some real solutions here. Here’s three things you can do to that’ll make you grow up fast and gain some confidence:

1. Figure out your strengths and focus on them. Are you a carpenter? Build tables and chairs all day while she’s at work. When she comes home she’ll be like, “WTF? Where’d all this furniture come from?” You can say, “I made it, honey. I’m a carpenter.” She’ll say, “Like Jesus?” And you can say, “Yes.” If she’s not a Jesus fan, start singing “Close to You” by The Carpenters and swing her around in your arms, then make passionate love to her on one of the tables you built.

2. Have you done something horrible to someone in your past? Call and tell them you’re sorry. Pick up the phone and say, “Hey, Janice, it’s Sidesaddle Sally. Yeah, I know it’s been like 14 years. Listen, I’m sorry about the time I pushed you off my balcony. I didn’t know my mom was going to walk in the room and she would’ve been mad if she knew you were there. She didn’t like your mom and told me to stay away from your family. Anyway, I hope your torso has recovered. Please accept my awful apology.” Accountability builds self esteem.

3. If you smell like shit, take a shower.

It’s pretty simple when you break it down. I think you should tell her you’re a little nervous around her. I know it’s not the manly thing to do, but the second you admit it, I bet the nervousness goes away. And, maybe she’ll become more aware of how you’re feeling and will do sweet things to make you feel comfortable. Oh, and be sure to get involved in activities that’ll build your self esteem– stuff that has nothing to do with her. You’ll naturally start to feel more confident and you’ll probably learn about yourself along the way.

Good luck, Sidesaddle.

The End.


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Featured artist: Charley McMullen is a cartoonist, comedian and filmmaker based in Ms. Tozer’s hometown of Pueblo, CO. His cult comic strip The Men from Cyclopolis is featured regularly on

About the Author

Amber Tozer

Amber Tozer is a stand-up comic and writer living in Los Angeles. She finds human behavior both hilarious and horrifying. Follow her on Twitter @AmberTozer

  • Sirena Gibson

    New favorite column

  • Drummstar70

    Amber you rock !!!!!
    I agree with you in response to that guy, Who is insecure about
    Dating an older woman…..dude… just be yourself ‘)’

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