June 2008

Here are your questions for June 2008.

Kevin from Armenia asks

I would like advice, What is the best way to handle a crush I have on a woman that is seperated from her husband???

Sissy says

Hi Kevin,

Sometimes that can be a very sticky situation because in some cases the couple gets back together. If that happens then you are stuck in an even worse situation. I think that it would be best to talk with her, get to know her a little better and see how serious she is about divorcing. You may also give her little hints that you are interested in her! Take it slow and just be careful!

Good luck


Dude23 from Western Cape, South Africa asks

Hi Sissy

I am 17 years old and have never had a girlfriend. There's this girl that I really like, and i'm sure that she likes me too, but my parents are VERY old-fashioned and will never let me go on a date with her.

What should I do?

Sissy says

Hi Dude,

If you are 17 your parents should not be restricting your dating. I would start a conversation with her and let it go from there. I would also have a sit down talk with my parents to explore their concerns and express yours.

If they see that you are mature, they should not have a problem with you taking a young lady to dinner or even over for a visit with them. In fact you may approach it from that angle, tell your parents you want them to meet someone that you like!

Good luck to you


Sarah from Virginia, United States asks

So I got into a relationship with a guy i've been waiting for since last year (he's a senior im a sophmore) but I dont want to be with him anymore. I love him and all but not the same as I used to. I also cheated on him and i'm completly without a doubt in love with the other guy.

Please help me. I need to break up with him and I dont want to hurt him.

Sissy says


Guilt and feeling sorry for the other person has kept many people in a loveless relationship. You do not want to be miserable so tell him that you are moving on.

He deserves to know and move on with his life. If you string him along you are not doing him a favor, just be honest and tell him that you want to breakup!

Good luck and move on to what makes you happy. Life is too short!


Kristina from NH, United States asks

Over the past 3-ish months I have become really good friends with this boy. This past month i realized I liked him as more than a friend. He also recently broke up with his girlfriend of 7 months.

I knew that he liked 5 people, and I found out a few days ago I was one of them. Today I found out he only like 4 people, but i'm still one of them.

He told my best friend that he likes me alot but doesn't know if he'll be able to have a relationship with me because i'm going to a private school next year.

I really like him more than i thought I could, and I know that he likes me the most out of the 4 people. but i'm not sure where I should go from here...

Sissy says


You need to just come right out and tell him that you like him and private school should not keep you from having a relationship. Have a conversation with him and share your feelings quickly before he moves on!


Amir from Tehran, Iran asks

Dear Sissy,

your advice has been so useful for me but I have some problems with my girlfriend. The problem is when we are with each other I dont know what to speak about and she keeps asking why I don't speak to her.

We have been with each other for a month and I used your pickup lines to get her number and I asked all the questions that I can about her and her life so please help me.

Sissy says


At least you have your foot in the door with her so to speak. Good job for that!

You will have to find something that you have in common with her (likes, goals...). If she starts a conversation be sure to keep it going.

Also look for things that are around you to chat about. This will help lighten the mood and give you something to talk about. For example, pretty day, new store, movie, sports... Compliment her and let that start a conversation.

Good luck to you and keep up the good work!


Will from TX, United States asks

I asked a girl who I work with out for coffee. I wasn't sure how interested she was beforehand, but the coffee and conversation went well, we went for a walk afterwards (her idea) and she gave me a hug at the end of all of it.

Sounds ok so far? BUT ... almongst that conversation she made a passing comment about her current boyfriend (I know she had a boyfriend before her current boyfriend). I pretended I didn't really notice ... but it left me confused and in a potentially awkward situation going forward.

I guess she made mention of her boyfriend for a reason, but why did she have a coffee, walk and hug with me? I think she is a friendly girl, but not a cheating type ... if the roles were reversed and I had a girlfriend, I know I would never want to create a situation like she did - yes, maybe she was just being nice, but it WAS misleading (intentionally or not???).

So what should I do now? I really like this girl and don't want to die wondering, but I am a genuine person and don't want to be hurt either.

Sissy says

Hi Will,

It sounds like she is interested in you and trying to figure out if you are as interested. She was trying to be honest, yet she didnt make a big deal of it to not scare you off. I would play it silent for a day or so and let her make the next move. Then when she does I would explain to her that I liked her, but was not willing to play second fiddle. It will then be up to her to make her decision and either dump the boyfriend or leave you be.

Hope it all works out

Sissy PS - be kind and do not stop talking or flirting with her, because you still want her to know that you are interested in a one woman - one man relationship.

Cryst from California, United States asks

Dear Sissy,

I've known this guy for a year now because I've become a freshman this year. I began to like him a couple of weeks ago, and its weird for me because I've been seeing him all year, and it hasn't occured before that I like him.

I've only gone out with one guy in my entire life, and since then I've decided to save myself for that special someone.

For this guy, I have an actual list of why I like him, and what are the things about him that makes me smile inside. He's everything that I could ever ask for in a guy but we hardly ever talk, and its awkward if I were to begin a conversation so suddenly in the year when I never have before (I'm the 'shy' and 'quiet' girl in my school).

I feel as if its impossible for him to like me because we never talk, and he's a senior while I'm a freshman, and there's probably many other girls he's dated before that are much pretty and smarter than me. And even if it all were to work out, he'd be at college while I'm still left in highschool.

What should I do?

Sissy says

Hi Cryst,

One of the first things that I want to address with you is a comment that you made in your post

"he has probably dated prettier or smarter girls"

It's important in dating to not set yourself up for failure and with that type of attitude you will fail!

We as people have to be reasonable and come to understand that there is always someone prettier, built better, smarter or whatever else, but that is not for us to tear ourselves apart over. Be proud of who and what you are.

Now with that being said it sounds like you need to ease in the situation. Maybe a hello, how are you today and tomorrow a little more "did you catch the game?". You are correct it would be terribly awkward to begin a lengthy conversation after barely speaking all year. A little at a time will do the trick - you will have to look for opportunities and think quick on your feet, but you can do that!

As for you still being in high school and him leaving for college, that happens a great deal of the time, but many people stay together, so don't worry about it!

Good luck and let me know how it turns out.


Josh from London, United Kingdom asks

I've been seeing this girl, she's Asian, 4 months now, taking it very slow, but still haven't even kissed yet...but thats about it, and I'm hoping to change that during the next date. She was out from a relationship when I came. Told me reasons was, the guy was seeing someone else.

Anyway, recently she mentioned seeing other guy(S). She's been open in telling me about it but actually spoke negatively about all of them. I've always played it off cool, showing her that I don't really care. but to be honest, I'm a little jealous now. I've never given her any hints of this and she tells me her friends say I'm nice compared to those other guys.

Of recent, she invited me to her house....it went quite normal, talks, laughs, slight slaps on the shoulders..nothing spectacular happened. I got my first awkward hug with her that day.

I'm very shy when it comes to dating... I've never had a girlfriend before or even been on more than a few dates with a girl (I just turned 22, so I'm sort of a late bloomer). When we talk, I'm always very confident, I make playful remarks, we both laugh a lot and our personalities seem to mesh well. I'm just shy when it comes to making moves. I've tried holding her hands on different occasions and it worked but after a while she just lets go (especially when we are in public).

What should I do? (besides the obvious of making a move on her...) she asked me if I've been seeing many girls and have some who are just friends, I told her I saw a few, but nothing has really developed (which is a lie... I haven't been on any other dates, but I thought it would look pathetic if she was seeing other guys and I was only seeing her)

My last post was about going in for the first kiss, and I guess I've come to the realization that I just need to man up and do it, i just don't know if I should do something beforehand (like try to hug her often... or just sort of surprise her with a kiss).

Guess I'm just looking for your take on this... I'm really really bad when it comes to dating (no wonder I'm still single at 22) thanks in advance for any responses!

Sissy says

Hi Josh,

At least you are progressing - I am proud of you.

This is not easy for anyone so don't be so hard on yourself. I would not surprise kiss her. As a woman I would like a little notice. You know that moment before the kiss where a man will stroke my hair or face. The lean in approach where you look into her eyes (does that make sense?).

If I were in her shoes and you seemed confident when we were around each other I would believe that you were playing the field because our relationship had not progressed. If you like her you have to make that move to kiss her. She may believe that you are dating others and not wanting to make a commitment to her. I know it sounds obvious, but you are just going to have to do it! You are at a now or never crossroads with this relationship.

As for her talking about other guys I would imagine that it is in defense for her beliefs that you are dating other women. She may be seeing other guys, but I somewhat doubt it. By four months others should not be in the picture, so I truly believe that she was seeing if you would get jealous!

Show some jealousy - a little is healthy and lets the woman know that you are interested in her and care.

I hope this helps you and good luck to you!


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