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Is it healthy to start a relationship with this guy after his GF dumped him?

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Question - (23 May 2010) 4 Answers - (Newest, 24 May 2010)
A female age 41-50, anonymous writes:

This guy I know, he's a friend of mine and recently was dumped by his GF. He says he loves her, but she treated him as crap after he had trouble in his finances over some bad decisions he took. The thing is the guy is broke and he realizes he has nothing to offer as to $$ concerns.

He says he's trying to get up looking for a job or start a business, so he thinks that's what his ex GF might take as consideration to take him over OR if "someone else comes in the way" and may want to start a life with him. He says he hopes by the time he can be UP again, he doesn't want her to come look for him again, so he wants to have someone else and be taken. I like him and he kinda feels attracted to me. Do you think I have a chance, is it OK to do it right now due his situation and if it's OK, what can I do to get close to him and make him know I'm interested?

View related questions: ex girlfriend, his ex

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A reader, anonymous, writes (24 May 2010):

This is verified as being by the original poster of the question

Thanks for your replies. I think is better how you say, I wondered b/c he flirts at me and people saying he likes me and I like him also, but if that's the circumstances I guess is better off that way!

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A female reader, YouWish United States +, writes (23 May 2010):

YouWish agony auntYou do not want to be a rebound with this guy. Nothing hurts more than when you fall for someone who isn't yet over an ex. Just give it some time and patience. Be warm and interested in him, but do not push the issue. You'll both when when he's healed, and you'll still have feelings for him. But you do not want the emotional baggage of an ex that he's not over.

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A female reader, BeSimplyTrue United States +, writes (23 May 2010):

BeSimplyTrue agony auntYou talked a lot about this guy, but what about your feelings in all of this?

How strongly do you feel about him? He's your friend, but are you attracted to him? You said you're interested--have you been interested for a while? Would you want to date him casually, or be a girlfriend/partner to him?

If you want to be a girlfriend/partner, do you think he's good boyfriend/partner material? It sounds like you're being understanding of his financial problems, but as someone who's been in a long-term relationship FILLED with $$$ problems, it's impossible for me not to warn you to consider this when you consider dating him. And no, it's not shallow. Spending habits often correlate with his state of mind, level of maturity, and priorities. A man who's depressed, young for his age (or just plain young), and/or is self-centered is a great candidate for money problems. Is this the kind of man you want to get attached to romantically?

All of that money stuff aside, I would say you should give this guy some breathing room anyway. It was "recently" that his girlfriend dumped him and he's probably still occupied with that. He'll need some time to process his pain, anger, and hurt pride. If you want a relationship with him, I'm guessing it would be nicer for both of you if he can focus purely on you and your developing romantic bond, rather than being preoccupied with her.

I'm sorry to be blunt, but what he said about wanting to be "up" and attached by the time she comes back looking for him sounds like his wounds are raw, his pride is at the forefront of his mind, and he's thinking selfishly. You don't want to be the victim of that selfish thinking. Breakups do make you selfish for a time, it's natural, but don't let yourself be the rebound if you're really serious about him. Let him know that you care, maybe even let on that you're interested, but I really suggest you keep him at arm's length for a couple of weeks until his head is in a better place.

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A female reader, Laura1318 Malaysia +, writes (23 May 2010):

Laura1318 agony auntI think it is not a good idea to start a relationship with someone who has just broken up.

Their minds and emotions are still not stabilized and they can make flip flop decisions.

Give them enough time for them to see the road ahead clearly before you start anything with them.

Or you could be a rebound relationship .

Well! If you think the time is right , you can show your concerns and interests in him in small ways.

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