“Normally, I would suggest making strong eye contact at first and see where it takes you, but as we all know, missed connections in major cities are bountiful,” says Serhant. “I would smile and just go for it. Give out a nice, genuine compliment. There is really nothing to lose in this situation, and most guys are impressed by outgoing women who know what they want.”

“When you run the risk of taking a chance on someone you work with or will have to see even if things don’t work out, the guy might keep things friendly just to avoid awkward encounters. If you really like him and think he likes you too, don’t be afraid to dole out some subtle hints—maybe a few light touches to the arm, some extra—but low-key—laughs at his semi-decent jokes, or you can ask him for help in some way, shape, or form. If he’s not brain-dead, he will catch on.”

“If he is calling, texting, or emailing after a date, then it’s safe to say he is probably still interested. Don’t be afraid to take charge (casually) and ask him what his upcoming week/weekend plans are. If that doesn’t prompt a second date invitation, then just let it sit a week or two without too much communication, then ask him out yourself. Men like the chase, and if you play a little coy, while also letting him know how good of a time you had, you’re bound to get him hooked.” But if he doesn’t take charge after that, just cut your losses and find someone more interested.

 

Flirting Tip 4: How to Ask a Guy Out Online

What’s the best way to make the first move on a dating site? “Send a nude picture!” says Serhant. “Just kidding…be genuine and friendly, and look for a commonality to talk about. Can’t go wrong with that.” If you draw a blank, a simple “hi” will do.

 

Flirting Tip 5: How to Turn a Friendship With a Guy Into Something More

“I wouldn’t beat around the bush at all with this one,” says Serhant. “As friends, you should be as open and honest as possible, but don’t put too much pressure on the situation&he might not have a clue how you feel. Carve out some time to talk calmly and privately, know what you’re going to say (but don’t prepare a script—let the conversation flow) and let him react before getting too far ahead of yourself. Just getting your feelings off your chest and out in the open is the important part.”

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Op-ed pieces and contributions are the opinions of the writers only and do not represent the opinions of Y!/YNaija.