Dating your roommates sister


Luckily for me, my roommate had the latter. To accurately set the stage, we need to go back two years prior to the night of our sexual encounter. I was out at dinner, and I was sitting next to one of my unfortunate pledge brothers, Buzzkill, and his dad, Mr. Somewhere between my fat filet mignon and another whiskey on the rocks, I heard Dr. My mom is one mean cuss, and it only gets worse when it comes to defending her children. She just about bit Dr. She was like a lioness who cornered her prey to maul his face. I had to buy her two rounds of tequila shots just to get her to calm down.

Fast-forward about one year and eight months later to the start of our junior year. It was SEC game day, and the smell of barbecue and bad decisions was in the air. She was at our tailgate with her whole family, including Buzzkill and his dad. My mom and I were getting our drink on and thinking of ways to passive-aggressively piss off the whole Buzzkill family. She would never admit it out loud, but part of her wanted me to hit on Horny.

To be honest, it was one of the easiest things I had ever done. I saddled up next to her at the tailgate when she did the unthinkable. She asked me if I wanted to come to dinner with her while grabbing my hand and pulling herself into me. I knew it was a bad idea, but, of course, I said yes. I am a gentleman, so I had to.

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After the game had ended, I went home to get showered and cleaned up. Horny showed up showing more cleavage than Kim Kardashian. Horny grabbed my crotch on the ride to dinner. After dinner, Horny kept grabbing my junk and tried to shove her tongue in my mouth in front of Buzzkill. That night, we went back to my place and lay on separate couches.

Dating Bestfriends Sister? - Relationship Advice

It was hilarious, I have to say, but the night ended innocently. We decided to go out one night to a bar for some drinks. Buzzkill had a big test the next day, so he was going to be studying at the library like he usually did, right? Find a place to interact with her. If you go to the same church, for instance, you may have an opportunity to ask her out after the service. If you go to the same mall to work, you might run into her in the cafeteria.

So, you need to think about possible opportunities to ask her out. Ask her out on a date. You need to be very specific when asking her out, so that she has something to respond to. For instance, you could ask her if she would like to go for coffee after class or if she is free to check out a movie on the weekend. I found an amazing coffee place on third street downtown that has this incredible Italian roast. I think you would appreciated it. Do you want to check it out on the weekend?

I think I like my roommates sister...

We are thinking of making the day of it, maybe bringing a lunch and trying to get in three or four climbs. Do you want to join us? Try indirect suggestions to ask her out. If you feel slightly awkward about asking her out directly, you could use an indirect method. I was considering a movie on Saturday night. Maybe you would like to join me after your study session?

How to Get Along with Your Boyfriend's Sister: 12 Steps

You might ask, "How are you feeling about your upcoming theatre production at Studio Y? But if you want to practice them some more, I would be happy to help out.


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Maybe we could grab a coffee and I could listen and give line prompts? Express how much you enjoy her company. Stalking is a bit harsh of a term to use for this situation. He seems to be obsessed with your sister for some reason maybe he thinks the only way he can meet a girl is through friends or family. It all seems very harmless at this point. Is there any reason why you haven't told your sister about this yet?

You should warn her about it so that she doesn't end up getting stuck in an awkward situation with the guy. Other than that this just seems like your average annoying roommate problem rather than anything you should be worried about. Can you, in a really nice way, confront him?


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And be like "Hey dude, I'm super protective of my sister and I get a little weirded out when my friends pursue her. I need you to lighten up a bit. Why not tell your sister that you think the dude is creepy and leave it to her to decide what to do. She's presumably an adult.


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Next time he brings it up, say something like "hey man, woah, leave me out of it. Look at his expression and body language for cues. He'll probably look a bit deflated once he understands that you're not going to help him out. Thanks, man, I knew you'd understand" and move on. If he brings it up again, throw your hands up and say: If she complains or asks about him, it is an entirely different situation, but until then, it seems best to limit your involvement.

dating your best friend's sister

Do what she wants. I'm seconding the idea that while this guy is taking a pretty unusual approach to finding a girl to the point of being a bit disconcerting , this behaviour is not the same thing as stalking. If it worries you then drop your sister a note saying that this guy seems to have gotten pretty focussed on the idea of meeting her just on the basis of her being your sister, and if she has any problems with him, then to let you know.

Beyond that, I'd let her make the decision for herself.

I do see this as a form of stalking. Warn your sister that this man is obsessing about her. Tell him that her personal life is private. Stop answering his questions about her. Move as soon as you can.

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