Find out what his status is. Try to gauge if he’s open to a relationship in general. Maybe he’s already got his eye on someone. Maybe he’s just had a horrible breakup and he’s not open to dating at the moment. You will need to respect him, his feelings, and the situation he’s in by not being overly pushy if he isn’t in the mood for a relationship. You may try to wait it out, but only if you're okay with just ending up his friend if it doesn't work out.
The punctuation you use matters as well. Research suggests that using periods to end all of your messages can make them seem “too final” and insincere. At the same time, an exclamation point has been shown to make messages seem more sincere. For example, there’s a big difference between the texts “I’m fine.” and “I’m fine!” when you’re on the receiving end. The first almost looks angry, while the other one seems light and carefree. Also, if you’re asking a question, always use a question mark to avoid confusion.
I know a woman who went out with a man she met on OKCupid. The chemistry wasn’t there, so they decided to be friends. He invited her to a party he was hosting, and she brought her friends. Now they’re all friends, and the ladies often ask the gentleman for advice on reading men. That’s a bonus in my book, to have a male friend who can give you a different perspective on dating than your girlfriends!
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