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Do I have a chance with this 40 year old bachelor? Or is he too set in his ways?

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Question - (2 June 2009) 5 Answers - (Newest, 3 June 2009)
A female United Kingdom age 41-50, *nteater writes:

I play bowls each week with 2 guys who are mates. They are both 40, never married and not had girlfriends for at least 10 years. They seem to be terrified of dating women. They are attractive and I have noticed women come on to them but it seems to go over their heads! I really like one of them but have no idea how to break through the barriers. Do you think its possible or do you think they may be too set in their ways/emotionally unavailable?

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A female reader, Anteater United Kingdom +, writes (3 June 2009):

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

. . .no they don't live together and pretty sure they are not gay. Just been mates for a long time. Both are introverted/shy. I suspect they don't have any confidence with women. I like the one guy because he's easy to talk to and I find him physically attractive. I know of other men like this and I'm sure its a confidence thing. He once said he has nothing to offer a woman. Maybe the motivation isn't there. I was just trying to get my head round this kind of mentality . . .

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A female reader, 48years  +, writes (3 June 2009):

48years agony auntDo these 2 live together?

Do they wear matching clothes?

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A female reader, Tisha-1 United States +, writes (3 June 2009):

Tisha-1 agony auntWhy do you like the one guy? What makes him appealing to you? Maybe you could try to work out what kind of women he finds attractive. But I am kind of thinking what the first poster mentioned as a possibility. Are they a couple? If you've got a friend with 'gaydar' see if she or he could scan him for that possibility.

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A reader, anonymous, writes (3 June 2009):

If they're terrified of women, then don't be terrifying! Figure out what he's afraid of, and don't be it. If you're approachable, fun, and easy to be with, it'll work out fine, provided he's in any way ammenable.

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A female reader, anonymous, writes (3 June 2009):

There is a reason that they have remained single for so long and I am sure it is best that you don't get hooked on one of them. Any man that has been single for that long is not good relationship material, why get your heart involved and possibly broken? Find yourself a good man!

BTW, have you considered that they might be gay?

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