Home Advice 8 Tips That Make For Super-Successful First Dates

8 Tips That Make For Super-Successful First Dates

No, but really — how does a person have better sex or a better relationship? The Fresh Toast has enlisted Rachel Krantz, a sex writer and proud canna-enthusiast, to help readers out with some answers as its sex columnist. No question is off limits, and all questions will remain anonymous. Please send your sex and relationship inquiries to editor@thefreshtoast.com. Now, onto this week’s topic: how to be smarter about first dates.

Q: I’ve been single for the past year. I’ve been doing a lot of online dating, but I feel like I must not be doing it right. The people I go out with seem nice enough, but either they don’t ask for a second date, or they do, and they turn out to be totally wrong for me — only I don’t find out until after I sleep with them and they reveal their true selves. What am I doing wrong? Is there any way to screen people better on a first date, or at least make it less of a waste of time if I’m not attracted to them?

A: Dating can be hard — everybody knows that. But it can also be surprisingly fun, an activity you use not only to find people to love or f*ck, but to get to know yourself better as well. As someone who’s gotten better and better at dating from the more secure position of being in an open relationship (it takes a lot of pressure off a first date) here are the things that have worked for me.

Take At Least Half An Hour To Center Yourself Before The Date


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If you’re just rushing to a date from work or otherwise hurry the getting-ready-process, you’re not going to be in a good frame of mind before the date. Personally, I like to give myself at least an hour to put some music on, get dressed and do my makeup, and take a hit off my vape. Those are the things that make me feel sexy and confident before a date — but it’s different for everyone. Find a routine that works for you, and make sure to try to check in with yourself mentally before the date: How are you feeling? What do you want out of tonight even if you’re not attracted to the person? Why are you fundamentally a good person even if they aren’t interested? Why do you want to meet someone in the first place?

Asking yourself these kinds of questions will help you go in with a clearer intention and more confidence. For example, last night, before a first date I was excited for, I told myself that my goal was to be honest, kind, to remember what a catch I am, and to at the least be open to making a new friend.

Consider Showing Up At Least 10 Minutes Early

Personally, I like showing up a little early. Having a few minutes to pick the spot I like best, to order my drink, and to otherwise center myself before the person shows up makes me feel more confident by the time they walk in. Warm up by trying to make conversation with someone next to you or the bartender. That way, you’ll feel braver by the time your date arrives (plus, they might desire you more if they see you talking to other people — friendly, confident people are attractive).

Pay Attention To Body Language


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OK, so you’ve met. As you begin speaking, if you’re interested, pay attention to their body language. Are they crossing their legs towards you? Finding excuses to touch you? If so, they’re into you, and if you are too, you can proceed with confidence. If you’re less sure either of you are interested from body language, don’t get discouraged — just keep it as information in the back of your mind, and don’t overstep what they’re signaling to you more than a few times if it’s not reciprocated.

If You’re Not Into Them, Use It As An Opportunity To Practice Kindness

It’s disappointing when you’re not interested in a first date — but it doesn’t have to be a waste of your time. Use it as an opportunity to practice listening, talking about yourself with confidence, and learning about something new. Consider whether they could be a good friend or work connection for you. If you can tell they are interested and you aren’t, practice treating them the way you would want to be treated in that situation. There’s a lot to learn from a “bad” date too, believe it or not — mainly, the kind of person you want to be.

Try To Hold Eye Contact To Build Tension


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If you’re both attracted to each other, staring into the other person’s eyes can be a bit intense, like staring into the sun. But if you can, practice holding their eyes for at least three seconds every so often — especially if they are talking about something important or you’re communicating a point you want them to remember about you. It’s hot, it’s intimate, and it will build chemistry that can explode later.

If they can’t meet your eyes back, they might just be shy — but it could also be a red flag for you that they are not as comfortable with intimacy as you are, and you can proceed with some more caution if you do choose to get involved.

Ask “Awkward” Questions


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Last night, I asked my date to tell me more about something he’d referenced offhand — how he was pretty sure his parents are in a sexless marriage. That led to a conversation about his mom’s addiction, his experience in childhood trying to help her, and how it’s impacted his relationships. I learned that he was indeed a kind, open, introspective man.

People tend to stick to small talk on first dates, but that’s a big mistake. Dig deeper, and you can get a sense of someone’s character and emotional intelligence much more easily. If something has been a deal breaker for in the past — you mentioned in your question that you often don’t find out until after you sleep  with someone — try to ask questions that get at that. So, for example, if a lack of ambition is a deal breaker for you, ask someone if they are happy in their work. If you have an ethical line in the sand, ask someone if they’re pro-choice or see the problem with eating animals. Whatever it is that’s essential for you, don’t save it for later in the interest of being polite. For more ideas of”awkward” questions to ask on a first date that can reveal a lot about a person, check out this other article I wrote.

Allow For Silence


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When I was younger, I used to fill even the slightest lull in conversation with a question. I wanted men to like me, and one of the easiest ways to do that was to get them to talk about themselves. While this wasn’t a bad strategy (it’s still good to ask questions!) you should pay attention to how the conversation flows between you two, and whether you’re the one doing all the driving. If you notice you’re the one who keeps asking questions, allow for that awkward pause, and see what they come up with. Chances are, the conversation will go deeper once they have a chance to say or ask what’s really on their minds. And if they can’t fill the silence, even after a long pause, be honest with yourself about whether that will be a problem for you down the line.

Think Of It Kind Of Like Being Recruited 


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Think of a first date as a job interview you’re going on even though you already have a good job — being in a positive relationship with yourself — and imagine the other person is trying to recruit you to join their team. That way, you’re not coming from a place of desperation, and you’re remembering that you are a catch. No need to be snobby or rude, just remember — you have options, and you’re not desperate. Let them sell you on why you should want to be poached away from the full-time job that is being fundamentally confident in who you are.

Keep checking in with yourself throughout the date, and remember: until you believe you’re a catch, it’s going to be hard to convince someone else who’s worthwhile that you are. If you find you follow these tips and you’re still having no luck, don’t blame yourself — but also see what you can do to get to know and love yourself better before you try inviting someone else in.

Good luck!

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