Expert: Dr. Dennis W. Neder - 12/8/2008

Question
I've known this certain girl for a long time and we've been loose friends for years. Recently I'd been wanting to ask her out, acting on long-ignored feelings, but I hesitate.

We have a lot of the same friends and if she were to turn me down or things didn't go well, it would be a mess. All our mutual friends would be privy to it and it would make things horribly awkward between us all from then on.

I think I have pretty decent chances with her, as I can sense some mutual attraction (I think...) but if it goes wrong, it'll be a big mess.

I'd like your take on this kind of thing. Should I just forget about asking her out (like I've been doing up 'till now) to spare the awkwardness among friends, or screw that and go for it?

Thanks in advance, your answers are always helpful.

Answer
Hello Jonathan!

Let's start with this: almost ALL relationships are messy (at least if they're worthwhile) - that's just the way it is. Very few of them start off all clean, white and pristine. If you're waiting around for the perfect time or situation or person or whatever, you're going to be waiting one hell of a long time.

Likewise, if you're over 15 years old, your friends are going to understand. It's perfectly natural for people to be attracted to each other - even friends. Have none of your friends ever paired up before? In these sorts of groups, it happens all the time and it's based on your level of maturity as to whether things get weird or not.

Remember, you're not professing your long-term, undying love here. You're simply "attracted". That's not a big deal, right? Right!

Now, the down-side:

You may very well have waited too long. Women have a natural, built-in mechanism to avoid guys that wait. It's the same mechanism that keeps them from dating their brothers! She may be attracted to you, but she also knows that if this has been going on for some time, you've been a coward about it by not moving on things when you first started to realize them.

These are cases where friendships work against you and I hope you carry this reality along with you the rest of your life. When you're attracted to someone DO SOMETHING ABOUT IT NOW. Don't wait years or you're going to lose that.

Here's what I suggest: since you know this girl well, just suggest that you and she get together (don't say "hang out"; it's a totally different - and wrong - thing!) away from the group just to get to know her. You're not putting your feelings out there, you're simply trying to see if you HAVE feelings! See the difference?

Next, get together with her and go do something fun, but make it all about "face time" with her. Don't go to the movies or a concert. Make it about you and her and really get to know her. Find out about her past and all the things you don't know about her.

Tell her that, "who knows?" maybe you and she will become an item and it'll be built right on that cornerstone of your existing friendship.

Likewise, agree that things aren't going to get weird between you and your friends regardless of where things go. If things doing work out, maybe your friends will help you get over this anyway!

Best regards...

Dr. Dennis W. Neder
President
~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.
Remington Publications
818.334.8826
http://beingaman.com
http://beingaman.tv
Publishers of "Being a Man in a Woman's World I & II"
Producers of "BAM! TV"