Several years ago I was in a relationship that ended because I was leaving overseas for several months. It didn't end well as she didn't understand why I left over her and for not showing enough interest to be clear on what I wanted from her. The relationship was short, but I still think about her often. I'm not sure whether to contact her and play it cool or just tell her how I honestly feel. Does age matter? I would play it cool if she were in her teens or 20's but she's in her early 30's. Do I tell her I think of her often and that my feelings never changed (and actually grew) or do I play it cool? Will a 30 year old woman think I'm a wuss for being vulnerable, admitting fault, and putting myself back out there or do I keep it casual and forget the past.

If you have not had contact then what makes you think she hasn't found someone else??

She might have had found someone else. Should I assume every woman I meet is already in a relationship? That's the chance you take.

I'm just trying to get a woman's opinion vs a man's opinion.

Most men will say "keep it cool and keep her guessing how you feel about her"

Most women will say "tell her how you really feel, what do you have to lose?"

Both approaches are opposite of one another.

Get the facts, and then decide which way to go. I have always looked ahead to the next adventure, but plenty of exes have haunted me over the years. What ifs and should have, could ifs, can drive you nuts.

Only one way to get the facts, and that's from her.

Sorry to burst your stereotype, I am female and I think you should either leave her alone or if you decide to get in touch with her DO NOT mention your feelings. Find out who she is today instead of expecting her to be the same person you left behind.

Are you the same person you were 'several' years ago? Don't expect her to be.

You ask, 'Should I assume every woman I meet is already in a relationship?' In this case, you aren't meeting her on the street or in a bar. She is an ex who has lived her life since you left. Yes, assume that she is in a relationship. Think about the possible fact of her having a husband and children. Are you so caught up in your 'feelings' you would cause problems for her in her life?

As Tal said, get the facts. Find out if she is single. If she isn't, do not complicate her life by telling her how you feel. If she is, get to know who she has become. Allow her to get to know you for who you have become. See if the old feelings are really still there before you hand her your heart. You might find out you are two very different people now and that you are in love with a memory instead of a woman.

This isn't a game. No points for 'keeping her guessing' or 'pouring your heart out'. Approach her as an old friend you want to get to know again or at very least touch base with. Don't allow impatience to cause you to make easily avoidable mistakes.

Cat1864, I appreciate your feedback. We're in a time where social media sites keep us updated/informed. Based on her profile pic, at a bar, without a ring on her finger, with a group of men and women (none of the men are with her), I can tell she isn't married with children.

What does "Don't allow impatience to cause you to make easily avoidable mistakes" mean? Just casually approach her and take it from there?

Impatience can cause a person to project his/her feelings onto another person and see things that aren't there or expect them to progress at a faster pace than is advisable. You think you know how you feel, but those feelings are based on your memories.

On-line Social Networks cannot give a full picture of who a person is in person. Pictures do not tell whole stories.

If you found her on a social network site, have you made contact with her or have you been looking at her profile and pictures building up stories in your own imagination of what her life is like now?

Take your time and get to know her.

Yes, if you want to contact, do it as a old friend, just catching up with them.

Again, not enough info on your age, and the age difference,
Not enough info on "how bad the break up was"

And of course, often what happens in old loves is we remember the good, and it is always better in our memory

So what's going on that you are seeking to reconnect with an old relationship that failed before, and ended badly?

And where do all these feelings you want to confess to her coming from after all these years?

Did you look for her on the social networks, out of curiosity, or NEED?

Or was it a chance discovery?

How long have you had these feelings?