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Simi In The City – A College Casanova and Bride To Be

When it comes to being in a long-term, and moreover, committed relationship, there are a lot of questions and thoughts which come forth. Simi takes on two in-depth questions from readers and we’re certain that there are more than just the two people who asked us these questions that are going through the same thing. Simi just hopes that you understand what is right and moreover, best for you, then take the steps needed to your happiness!

Happy reading!


Simi, not sure if you get a lot of messages from guys, but here we go. I’ve dated a lot of girls since high school and throughout college. My longest relationship with a girl was close to three years and that ended just over a year ago. Since then it has just been casual dating. I am looking for something serious but everytime I do I always keep coming back to my best friend’s sister for advice. She’s known most of the girls I’ve dated and always gave me her two cents, whether I wanted it or not. We messed around when we started college but that was it. I’ve always been attracted to her but she’s my bro’s baby sister. Really, what is the fine line between dating your best friend’s sister or even more than dating?

College Casanova

Dear College Casanova,

First off, congratulations for being my first official response to a guy! It’s going to be a different perspective coming from me to you, but hopefully it gives you some insight. Now, after recovering from a three year long relationship, I can imagine why you are responsible enough to be searching for another commitment like that again. Not sure why you’ve been unlucky turning any of the casual dating to something more serious but I can assure you one thing: at the end of the day, EVERYONE would love to have a relationship that started off as a friendship with years of time invested into it. Whether it be your best friend’s sister or his cousin or his aunt is irrelevant- a friend you can share your innermost feelings with and trust to give you their two cents is a friend you definitely can’t let slip away. Sure you’ve messed around a couple times, sure you’ve always found her attractive; but bottom line is she is a person that you can see yourself dating at some point in time. There is a fine line to be noted in between the dating of a best friend’s sibling, but there are easy ways to mind the boundaries. If you are truly interested in getting to know her further, the first and foremost (and possibly smartest) piece of advice I can offer is to bring it up with your best friend. At first he may be taken a little by surprise, but if your intentions are genuine, there would be nothing stopping him from approving. Although it will take a little getting used to, I’m sure if both parties are happy, that’s all that would matter to him. With that being said, I would be very careful with the waters you tread on- meaning you have to be more than careful to keep your relationship with her and your relationship with your best friend separate. Never involve them two in matters that don’t involve them directly, always be mindful that although they are blood, they are still two different entities. If you play your cards right, this can be a very beneficial move in your life: good luck!

Hey Simi! Me and my boyfriend (now fiancee) have been together for 6 years. I always told myself that I would stay a virgin till I was married and I am 29 now. He has slept with only one person before me and lately he’s been trying to persuade me to sleep with him and saying that “it will be ok” and “we’re going to get married soon,” but our marriage is still another 5 months away and I would like to wait till that. What should I do? I don’t want to risk anything happening…if you know what I mean?

Confused Bride 2 Be

Dear Confused Bride 2 Be,

This is quite a heated subject (literally, ha-ha), but I definitely thank you for being so straightforward! I have actually dealt with this issue personally, and I applaud you for staying true to yourself until 29! Now that you guys are so close to marriage, I’m sure the excitement and anxiety of the new chapter to come has got you both chasing thoughts. On your end, you’re still interested in keeping your values upheld and to preserve the sanctity of marriage- on his end, I’m sure he’s just being a normal guy, wanting all of you! Neither of you are wrong in what you want, you both just have different ways of thinking about the situation, I’m sure. Explain to him how this added pressure of going back and forth on your decision is not something that should be dealt with. I’m not usually biased, but in these situations I tend to side with females more often than not, because I’ve been in the exact same situation. Stand your ground; and explain to him that yes it may be an old fashioned thought, but he should love you enough to respect your wishes. When you both come to a mutual compromise and stick to it, imagine how much more exciting that first day after your married is going to be! Definitely something to look forward to on his end as well as yours, and at that point I think he will be very appreciative and actually respect the fact that you stuck by your word for so long. It’s a great feeling to have someone that accepts you for exactly who you are, and is willing to stand next to you for your beliefs. Take care and have a happy married life! XOXO.