If your experience in the dating world isn't at least a little bit awkward, you're doing something wrong.
Especially in a relationship that's only a few months old, there are bound to be hurt feelings, and embarrassment, and confusion. When do you tell the person you're seeing that you'd like to be exclusive? Or that you're just not into them anymore?
There are no easy answers, and we're not pretending to have them. But for some nuanced insight, we consulted relationship expert Andrea Syrtash, author of "It's Okay to Sleep With Him on the First Date," about how to navigate some of the most uncomfortable dating scenarios.
Read on for Syrtash's top tips on dating with confidence.
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The awkward situation: You want to ask someone you just met on a date
What to say: "I would love to get to know you. Would you be open to going out for a drink with me?"
Before you extend the invitation, Syrtash recommended looking for a ring or any other indicators that the person is currently unavailable. But if you can't see anything, don't ask, "Are you single?" They'll let you know.
Make sure to be confident and friendly; keep your body language open; and maintain eye contact. In this situation, your delivery is just as important as your language, Syrtash said.
Remember: Worst-case scenario, they'll decline, and you'll probably never see them again.
The awkward situation: You want to ask a good friend on a date
What to say: "I need to tell you something and I feel a bit vulnerable right now. I would love to take you on a romantic date — not a friend date — and just see what happens. Would you be up for that?"
This scenario is a bit more high-stakes than asking out a total stranger, because you don't want to jeopardize your friendship. That's why Syrtash recommends trying to suss out whether your friend might be interested in you, too.
For example, if they only invite you over to build furniture and they're always talking about their crushes, you might want to ask yourself if it's really a good idea to ask them out.
Another tactic Syrtash recommended is dropping subtle hints before inviting them on a date. Start with some gentle touching — maybe put your hand on the small of their back — and try to be a little more flirtatious. See how they respond.
The awkward situation: You're not sure who should pay on a first date
What to say: Nothing.
Syrtash advised against talking explicitly about who's going to pay. (It kind of kills the romance.)
In general, Syrtash believes that whoever initiated the date should pay. The other person should accept graciously.
Interestingly, among her clients, she's noticed that most women who date men do still expect the man to pay. If you expect the other person to pay but you're planning the date, try to pick a place that isn't so expensive so you won't feel guilty when your date foots the bill. Syrtash suggested arranging a date over happy hour drinks.
When the bill arrives, even if you expect the other person to pay, you should still offer to pay and know that your date might agree to split the cost.
And if your date does end up paying, make sure to thank them — even if you weren't feeling a romantic connection.
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