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You can NEVER second-guess someone else, so don't start now. You have no idea how he truly feels about you, but obviously he cares for you. I'd simply ask him over for dinner to start with and, in one of your conversation you could say "We've known each other for quite sometime so what do you think if we go out on a real date like other couples." He may go for it or he may need head space for some reason, but this certainly doesn't mean a relationship couldn't occur in the future. Take it slow and easy. If you don't try you could be missing out on a beautiful thing. Good luck Marcy

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Q: How do you ask someone out if the person liked you for so long but is now on his own?
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