Just relax and have a good time, remember to follow through with your flirting when you meet him in person the next day! Maybe you’re new to flirting and don’t quite know where to start, or maybe you’re an expert looking for a few new tricks. If you’re unsure, just tack on a smiley face at the end of a text, or even a winky face if you’ve said something a little flirty. If he seems to be responding to your texts fairly quickly (within a few minutes) and with decently long responses (a sentence or two), he is engaged in the conversation. If he’s sending a lot of one-word texts or just barely answering your questions after a long time, he’s probably not interested. For example, if you both love the same band, ask him how he feels about a new single, or which of their songs he likes the most. You don’t have to ask him out on a date, but maybe mention a concert that’s coming up soon, or a great coffee shop that he just has to try.

Even something as simple as “We should meet up for coffee sometime!” might get the message across — you want to spend some time with him. If he is really into a sport that you have never heard, maybe ask him to watch it with you and explain!
If you flirt with him through text messaging, try flirting a bit when you see him in person.
If you're a hot flirty chick over text message then hide in the corner because you're shy when you see each other in real life, it will send mixed messages! Although it seems a little cheesy, people like using smiley faces because they imply flirtiness while still being a little innocent and mysterious. In texts or chats, you can’t pick up these cues, so emoticons come in handy to help clarify your intentions. For example, if you started the conversation asking what the English homework is, try asking him what he thinks of the teacher, or what other classes he’s taking.

His favorite article he’s worked on is How to Change an Accu Chek Spirit or Combo Insulin Pump Cartridge and taking the photos to turn it into a Featured Article. Start mildly, maybe with a “You have great taste in music!” Or, after he says something funny, send him a “Hahaha, you’re really funny!” A little ego boost can go a long way.
He’s most proud of helping to overhaul the wikiHow Tour to make it more helpful for new editors. Asking a guy questions about his life will probably be much more enjoyable for him than hearing you blabber on about your own. If you can’t think of anything specific to say, ask a question about class you have together, or even how their day was.

Why won't he ask me out again
Im dating an old married man
Annoying boyfriends are better
If a married man loves you

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