How to get a free weekend on

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My question is: How to get a free weekend on

My 2nd question is: I have a great group of girlfriends that I should be asking this question to, but I just feel like, since they know the guy, can't possibly be objective..

I am a teacher who lives a few hours from the town where I grew up, but I remain very close to my family and all of my friends who still live in my hometown. I went home to visit last week for a few days, and went out alot with my big brother and all of our mutual friends. There is this guy who is pretty good friends with my brother, and since my brother and I are close, I have known him(we'll call him Kris) for a while. Kris and I have always been flirty but in a friendly way, and he always seemed a little to immature and goofy for me to ever consider dating. About a week ago though, we ended up all going out together, and at the end of the night Kris and I ended up having a great kiss. We didn't tell my brother because, even though we are both adults now, he tends to be very overprotective, and it's just not worth telling him unless it's going somewhere. I have since returned back to the city where I work, but Kris and I have been talking everyday, and something about that way I think of him has just changed.

I don't want to sound pretentious, but Kris is just not typically the type of man I would be interested in. He is a year younger than me, enjoying life as a grad student, and I always just thought he was pretty immature. His life revolves around (occasionally) going to class, partying, and playing golf. I typically date using much older, wealthier, more attractive men. But I can't stop thinking about Kris, and how it's so easy to laugh and be myself with him. Some of my friends tell me I'm "out of his league." He is certainly looks nothing like the men I am usually interested in, but he's fun, warm, and eager to listen to everything I say. It makes me cringe just to say that because it sounds so stuck-up! And in reality, these older successful men have always left me lonely, or unhappy, or feeling used. .

He has talked about traveling to see me again, and I just don't know if it's a good idea. My brother adds pressure as well because he would never approve of me having something casual with one of his friends, so I don't want to deal with him unless I know it's going somewhere. I don't know if I am just interested because I can tell he really likes me and hangs on my every word, or if I truly am attracted to him. I haven't had such great conversations with a man in a very long time, but sometimes when we talk it's clear we are at different stages in our life. I am still young myself and while I am not looking to get married anytime soon, I would like to get out of the single scene and find a healthy stable relationship. I am afraid the party girl that I was a couple years ago  would be better suited for him.

Please help!!!..

Comments (5)

Hi Margot,.

Welcome to the board!!.

I think you've answered your own ?.  The men you have dated in the past have not been successful and you feel comfortable with Kris.  I don't think it will hurt to go out with him a few times.  Don't put so much pressure on the whole situation and push him to say this could go somewhere.  You don't even know that yet.  It takes time to know that about another person.  I think it would be okay to discuss with Kris the brother factor in all of this..

In regards to his maturity level.  He's not quite to the point where he has to prove himself.  he's in school still.  He might not change much, but he's coming to a point in life where this will all be seen..

I'm learning this myself, but to have love is a big risk.  We have to decide if we can handle the risk..

Good Luck,.



Comment #1

It seems that you are in the mood for a little hanky panky with a guy who you would normally dismiss.  If you can enter into this with an open mind and just enjoy his company without pretense then you might have some pleasant memories later in life about your time with him. .

I know you want to exit the singles scene and settle down with a healthy relationship.  There's nothing wrong with dating (online dating with that doesnt have an agenda, structure or a purpose...sometimes you just need to experience *people*.  I know it sounds kind of free spirited but sometimes you just need to *live* and not worry about where everything is going all the time.  If you dont focus on that outcome (settling down) so much you'll find that the time flies much faster that way when you are enjoying yourself.  Since there is no one around who you would like to settle down with, why not enjoy Kris's company?.

You do sound kind of stuck-up about yourself, but maybe it's due to the people who you have surrounded yourself with up until now. ..

Comment #2

Thank you so much to both of you for those wise words. I am new to the board and I appreciate your welcome and your honesty. I think you are right to just keep it relaxed and see where it goes.  If anyone else has input I would love to hear it.

I understand I might sounded kind of full of myself with how I described the situation. I hope I can prove that I'm not by continuing to discuss stuff with everyone Thanks again!..

Comment #3

"I understand I might sounded kind of full of myself with how I described the situation. I hope I can prove that I'm not by continuing to discuss stuff with everyone Thanks again!".

Dont worry about it.  Everyone toots their own horn sometimes...

Comment #4


It sounds like you rely on others too much to decide what is best for you - esp. your brother.  Part of that comes from your age and another comes with not having a fully developed sense of yourself yet. At the end of the day, while we want the people we love to like and approve of whom we love, what matters most is being truly happy and content with ourselves and the people we choose as partners.

The thing about 'types' is that while there is likely some common thread there that we gravitate to, if your standard 'type' is with men who do not stick around or whom otherwise, you haven't had a much luck with, then you need to reassess what makes them your 'type'?  For a long time I was attracted to worldly men - but they really aren't right for me - I'm much more at ease with down to earth types because that is what I am. What I liked about the 'worldy' men was the sense of adventure or playfulness in them. When I opened my eyes and my heart I saw teh difference. This could be your case as well - find what you are really attracted to about your typical type and look for those qualities in other kinds of men - including Kris.

Don't get so caught up in what other people think or in 'types' that you miss the possibilities that are presented. Sometimes teh best opportunities in life are served in the least obvious ways. You are the best judge of what is right and best for you - no one else is an expert on you but you. Listen to what is in your heart always - it will not lead you astray - even when everyone else questions you.



Comment #5

This question was taken from a support group/message board and re-posted here so others can learn from it.


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