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 OK 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.
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 will 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 will 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.
The awkward situation: You'd like to be exclusive with the person you're seeing
What to say: 'I really enjoy spending time with you and I'd love to do it more. I'm not comfortable if you're sleeping with other people and I figure that's worth bringing up now. How do you feel?'
Syrtash cautioned that it's not a great idea to have this conversation on a first or second date. But once you feel like you two are 'dating' -- whatever that means to you -- it's ok to bring it up. Remember: The person can't read your mind.
The key here is to stay positive and to confidently assert your needs -- instead of being accusatory or putting the other person on the defensive. So don't say something like, 'Don't waste my time.'
The awkward situation: You feel like the person you're dating wants more from the relationship than you do
What to say: 'I'm having so much fun and I want to be open about the fact that I'm still dating others and I hope you are, too.'
You don't need to give a long explanation for why you're dating other people, Syrtash said.
But be prepared for your statement to open up a bigger conversation. The person might get defensive: 'Well, I'm not looking for (an exclusive relationship) either!'
Or, the person might tell you they were hoping to be exclusive -- in which case, that's good to know now.
The awkward situation: You're not sure how to tell family and friends that you and your partner met through a dating app
What to say: 'We met through an app and hit it off.'
Plain and simple. If people get uncomfortable, Syrtash said, that's their problem -- not yours. There shouldn't be a stigma attached to online dating.
Again, it's all about staying confident. If you say it sheepishly, Syrtash said, you're inviting more awkwardness than is necessary.
The awkward situation: You run into an ex while you're out with your new partner
What to say: 'This is super awkward, but my ex is here. Can we move? I just don't feel like talking to him/her.'
The bottom line here is that you don't need to invite your ex into your date, Syrtash said. Either exchange brief greetings or move so your ex can't see you. There's no need to cause drama.
When you let your current partner know that your ex is in sight, you can even laugh and make a joke about it -- hence the phrase, 'This is super awkward.'
Either way, be aware that this situation might open up a conversation with your new partner about your last relationship.
The awkward situation: You just called your partner your ex's name
What to say: Laugh and make a joke.
If this has happened once or twice, don't overthink it, Syrtash said. Laugh and move on, or don't acknowledge it if you think your partner didn't even notice.
If it's happening all the time, you might want to ask yourself what that's really about.
The awkward situation: Someone's breaking up with you after a few months, and it's a total surprise
What to say: 'I was on a different page. It would be helpful for me to know how long you've been feeling this way.'
Syrtash emphasised that there's no one, blanket statement that can make a breakup less awkward for the person on the receiving end. Even if you do have a stock answer ready for the moment, you'll probably be so upset that it won't come out right.
But Syrtash said it's ok to ask some questions, such as the one about how long the person has known they wanted to break up with you or, 'Can you identify why you don't think we're compatible?' It's also ok to express that you're feeling disappointed.
At the same time, it's not always appropriate to ask, 'Is there someone else?' You may not get an honest answer.
The awkward situation: You're breaking up with someone after a few months
What to say: 'You deserve to be with someone who brings out the best in you. I don't think we are bringing out each other's best.'
Another option here is: 'I want the best for you and I don't feel that I can provide it. I feel awful because I care about you a lot, but I need to be honest.'
Oftentimes, Syrtash said, when someone's getting broken up with, their instinct is to show the other person how great they are. Remind them that you're not bringing out their best, and that the relationship isn't healthy for either of you.
As hard as this is for you, remember that it's hard for the other person, too. That's why it's important to be patient, and to listen and be kind.
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