Ask Roulette

Welcome to Ask Roulette. A different kind of advice column. All questions can be submitted here!

This is for entertainment purposes only. All advice received should be recognized as unprofessional advice from a professional smart ass. Also known as really good bad advice.

As always, love and sex questions pretty much make it to the top. Would you expect anything less?

Seems like the running theme this week is relationships and communication. Which is fitting considering the dating mess I’ve had over the last three weeks. I hate that other people are going through these things, but I’m kind of selfishly glad I’m not alone.


Dear Roulette, 

Ok. I’ll play. A KY. girl comes to the store, we chat. I chat with everyone. I’m on the job. This goes on for months, but one night is different. She has been out with friends, she has had a few drinks. She begins our usual conversation differently. She is lonely. Her friends have children. She doesn’t fit into their group. She says its time that we were formally introduced. She works the grave yard shift. She continues with how much she drinks, the music she likes, the new neighborhood she moved next to. I may have this all wrong. I did not get her phone number. My bad. I just don’t expect this kind of attention at work. I may never see her again. I am not the stalker type. I have tried to find her on space book, but she is not a fan. She called it fake book. Just like me! Even if everything goes over my stupid head, I still would like to find out. There is certainly a vibe going on. Shit, if she just wants a friend, I can do that. Am I just supposed to wait for fate to bring her back to my place of work? Why did I not pick up this earlier? She gave me many chances.  Am I just too stupid? 

Nothing to Lose

Dear Nothing to Lose, 

You should definitely become a stalker. If you can’t find her on Facebook. I know a girl. She’s a close personal friend and can find any person, anywhere (along with their marriage record, divorce record, financial history, criminal background, and blood type just in case they need an organ). But honestly, I wouldn’t worry about her too much. Fate keeps putting her in front of you, it will do it again. I would be surprised if you haven’t run into her by the time this blog is posted. I am excited about this new love (or friend) of yours. Life is too short to wonder. So if you get the opportunity again, seize it!! Get her number, invite her over, take her out… Just do something!!!! 


Dear Roulette, 

Is it still possible to get friend-zoned although you‘ve fucked her many times?


Dear Curious, 

It is absolutely possible to get thrown in the friend zone after sex. Sex doesn’t make a relationship. Even if the sex is good, there may be other characteristics she wants in a man that you don’t have. And depending on the conversations that took place prior to sex, she may not know you want more. If it’s not all about sex, you need to back up on the fucking and step up your game to show her you are a man. Have a conversation with her. Communicate what you want. Take her out and show her that you are happy to have her on your arm in public as well as in private. Women are not mind readers (even though we typically do know everything). Good Luck! 


Dear Roulette, 

Is it right when your girlfriend/boyfriend ask about how many people you’ve had sex with in the past before you met her/him?

Not Sharing

Dear Not Sharing, 

That’s going to be a hard no from me. I prefer to not talk about my sexual past or my past at all (unless he stumbles upon the blog then he will know those dirty details). I think it is fine to ask the important questions. When was the last time you had unprotected sex. When was the last time you were tested for STDs, but other than that, your past is the past, it’s not a reflection of who you are with him. And it rarely will help your relationship unless you are a virgin. That’s the only time you get an A+ on that answer. But that road goes both ways. If you are one of those people who insist on knowing all the details, you need to be prepared to divulge all your dirt. Which is another reason I stay far away from that question. I’m pleading the fifth every time. 


Dear Roulette, 

What is the difference between a date and two friends going out? 

In the zone?

Dear In the Zone, 

There is a clear difference in a date and two friends going out. First and foremost would be the premise of your outing. If you are questioning the relationship, you need to go ahead and handle that conversation. If you are out on a date right this minute and you haven’t handled it, here are some clues: the other person talks about their dating life with no regard to your feelings, they go dutch (if it were a date, he would pay), there is no playful touching across the table (or next to if he’s sitting next to her which would also indicate a date). And most importantly, the goodnight kiss. If there is one then you know…and maybe don’t use the word fucking about someone you care about…

See you next week!


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