A personal dilema
 

I am having personal issues with asking this girl out. Let me tell you the situation...

I am a 26 y.o. male with 2 great kids. I am recently divorced and have full custody of my kids, they live with me full time. I am the nice guy that you guys all say that finish last, my wife cheated on me with one of the bad boys, so in that respect I guess I did finish last. However... that isnt the point of this topic.

This girl, who I have my eye on, is my sisters best friend. She is 21 and has been around my family forever. She even works at my family business once a month and that is my favorite day out of the month.

Well besides the fact that I am natually shy, the one day at work I heard a customer comment to my sister that he thought I had the hots for the girl in question. My sister says, "No, she is like his little sister, he has known her forever."

Now I feel like I shouldn't even be looking at her now....

So my question is, should I even attempt to ask her out? If it doesn't work... i'm sure it will make things awkward.... but... I like her... alot.......

sigh

Any advice??

thanks in advance

Toast

Life's a risk, man. Every day you get outta bed, you're setting yourself up for one big fall.

And you know what happens? You can usually make it home ok.

If you're just lusting after her, or have some juvenile crush, I'd say let yourself cool off and don't risk any awkwardness. After all, that kind of age and maturity difference leads me to believe that you two probably wouldn't be on nearly the same level. She's 21; do you honestly think she'd want to get involved with someone who has two children? I can tell you, being about that age, that not even a bear trap would keep me in a situation like that. But, that's me.

Then again, there's no better time than now to toss the dice. You're young, you sound like you're doing well, so why not? The worst thing that can happen is she'll say no and your sister will chide you for a few weeks.

its to close to home on this one, continue to enjoy the young lady as a fantasy, This situation is just not/or won't have a happy outcome if explored any further.

Hey life's a dance. You learn as you go. Sometimes you lead, sometimes you follow. Don't worry about what you don't know.

Ask!

The worst that could happen is she will say "no."

But she could just as well say "yes!"

You are young, the worst she can say is no. If you really like her you may even try 2 or 3 times. You will probably be happier in the long run if you give it a shot.
From experience when asking out a friend or someone who is kind of a friend, try not to be awkward when asking, and expect it to go slower than normal.

I was in the same situation, asked, asked again and asked a third time, finally a yes. It looks like it is towards the end of the relationship now, but I am happy I tried, and would do it again.

Better to risk rejection than to sit around watching TV by yourself, wondering about the one that got away because you NEVER ASKED HER.

What lurkette said... You'll never know if you don't ask. Sure, she might say no. But isn't that better than wondering?

Come in from a friend angle. If the attraction is there and mutual, then it'll happen.

Hey that's just your sister's opinion not her friend's. Just be straightforward and ask her out. No games, no bs. See what she says worst case scenario she stabs you with a steak knife. Oh wait I mean she says no.

If you're actually serious about it, start hanging out with her. Go places with her. I'm sure you can do it easily considering you're such long-time friends. Just keep in mind your sis might get pissed at you for doing her best friend. They tend to not like that so much, from what I hear.

Good could possibly come out of this situation.


What I would do:
I would ask what your sister thinks of the idea of you two together and it she thinks it could work. They're best friends, right? So she would probably know what the probable outcome is of the situation and how her friend would take it if you asked her out. If you can get her support, or at least inform her of your interest in her best friend, she'll probably stop referring to her as something "like a little sister." That alone could probably improve your situation and chances. Maybe she can give you tips on what's the best way to ask her or what kind of hints to leave or if you should just be direct. Anyway, I think talking to your sister before you do anything might be advisable. That's just me, though. If she disapproves, do what you think is best in your heart (better to take a chance than to regret not doing so).

"You can do it"

... "all night long" :D !!

Go For It !!!

I'm tired of hearing "The worst that could happen is she says no." In this case, I don't think that is the worst. There is the possibility of losing a close friend. If she thinks it's weird, she might not want to hang around as much. I would much rather keep a friend than risk losing it for an intimate relationship.

I agree with motdakasha. I think the best way to deal with it is to approach your sister first. Find out what she thinks and if she's cool with it, she'll probably even help you out. Hopefully you're close enough with your sister to talk to her about it.

Analog has a good point too. You don't have to ask her out quite yet. Just hang out with her a bit more. It might be strange to her if you ask her out with no warning, especially since you've known each other for so long. If you've been have been hanging out with her more, and doing things together it won't be so awkward.

Go ahead and ask her. I would maybe mention to your sister that you do like this girl. If she thinks she's been left out of the loop she might get upset with you. Let your sister know that you wanted to be open with you on this since it's your sister's friend.

I know growing up my best friend had a hot brother. He treated me like a sister and even called me sis. I had a crush on him for years and never even told my friend. You never know Maybe she already likes you too.

life´s a gamble, roll the dice!

I once knew a girl who I always thought of as just a friend. That's not how she felt about me, but I didn't know it. I would have gone out with her if she'd just asked, and I think we would have had great times together. But by the time I figured it out, it was too late (would have been weird for a couple of reasons). I wish I had known.
If she's a close friend, talk to your sister about it first, and I think the worst thing that could happen is a "no". She might think it's strange that you're (a long time, close friend) interested in her, but she won't dislike you for it.

I would agree that asking your sister for her opinion first is probably a good idea. She would know her a little better than you, and she would probably know if she was seeing someone that you don't know about. Maybe get your sister to plan a small get together so that you hang around her more than just at work. After a while of that maybe just ask her out as friends, maybe dinner and a movie. With your recent divorce I'm sure she's aware of, just tell her you would like to get out and do things again but just as friends. As far as someone mentioning the age difference 26 & 21 is not that big of a deal, however her age and your two kids might be. I was married at 19 and I was ready by the time I was 21 just hasn't happened yet, (now 23)but some people aren't ready at that age. That might be something to ask your sister about also. How she would feel about dating someone with kids. Hope all works out for ya.:)

It's better to have loved and lost, than to never have loved at all.

It's definately worth a shot man.

Go ahead and ask her out.

If my friends had listened to what my sister said, they wouldn't be happily married today. Nobody can dictate to you what your life should be. It took me years to finally realize that I had done enough in my lifetime to please others and that it was time to live for myself. There are so many things that you don't do in life to avoid hurting others, but this does not apply in this situation. Either it works or it doesn't. I say go for it.

It's better to get a feel of the situation through someone who knows the girl better than he does. He doesn't have to follow her, or our, advice word for word.

I would definitely talk to your sister--who knows, maybe she's in the lady's lounge asking other TFPers the same question but in reverse. But if your sister says that there's no chance, there's no chance, she's out.

I'd go with what some others have said and talk to your sister about it. Your sister is going to love you no matter what, and even if she finds it a little awkward at first things would get back to normal very quickly. Best of luck with it.

Keep us posted !

I'd say do some research, with increased time spent, perhaps asking your sister in a subtle manner - if the vibes are bad then there's no point putting yourself in for a potentially very uncomfortable situation by asking her out. I'd err on the side of caution if I were in your shoes.

she already knows you which is the first step...after that just approach her and let her know how you feel
:cool: