5 of Your Most Embarrassing Dating Questions, Answered

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Most millennial women have gathered around a brunch table or dirty bar to discuss the Big Questions that come with dating. You know the ones I mean—the ones we all experience (sometimes over and over) but for which we can, for some reason, never really find a single, works-every-time answer. But still, we can never get enough wisdom, ideas, and theories that can help us navigate those inevitable relationship quandaries.

To give you some important tools for your adulting arsenal, we canvassed women for the dating questions that they’ve never quite figured out. Then we reached out to experts for their input. We discovered that, while there may not actually be a one-size fits-all answer to our most earnest questions, we do have some A-plus advice that will at least shine a brighter light on the murkiest (and at times embarrassing) dating questions.

On Pursuit

Q: “How much should I pursue a relationship? How much should I hold back? How to answer: Should I text him or her, or wait to be texted — and for how long? –Taylor, 28, New Jersey

A: “Don’t play games. Be yourself. If you’re not sure who that self is, or what you want in life and relationships, then focus on finding out, rather than texting strategies. Think about it: If you haven’t figured out who you are, how can you find someone who’s the right a match? When you come from an authentic place, no matter how you communicate with people you’re dating, you’re acting out self-respect, rather than a place of fear. If you like someone, you can show that person. And at the same time, always have your own life filled with friends, passions, and hobbies. I think there’s a difference between ‘she’s hard to pin down and get a date with’ because she has a full life versus ‘she’s playing games and being coy.’ Your behavior — texting and otherwise — shouldn’t be centered around another person, and how you hope or fear they’ll perceive you. And ultimately, at the end of the day, you should choose to spend time with someone because you want to be with that person — not because you can’t live without that person.” –Nicole A. Schaffer, Ph.D.

On Being Pursued

Q: “How much effort is enough effort to receive? How do you know when it’s the right balance? If a person likes you, will he or she really do anything, or do whatever what it takes to be with you — or are people sometimes just busy with other life things and not prioritizing relationships?” –Rose, 26, Queens

A: “You have to ask yourself: Do I want someone who makes their relationship a priority? If the answer is yes, then he or she should be making efforts to be in touch regularly and clearly stating when they want to see you and making that happen — not to mention making it clear how much they like spending time with you. If they really like you, they’ll want to be with you, and their efforts will match. Let people show you who they are and what their priorities are based on their actions, not just their words. Remember, people generally show the best side of themselves during courtship, when they’re out to impress and before they’ve gotten too comfortable. Try to project out and think about what it’ll be like when things get more difficult or less exciting — as life tends to do. If they don’t make efforts in the beginning, it’s not going to improve later.” –Sharon Sommers, PsyD

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MORE: 9 Things Everyone Deserves in a Relationship

On Being Ghosted

Q: “Why did he or she ghost? How can I avoid being ghosted on?” –Every single girl we asked for questions

A: “First of all, recognize that being ghosted doesn’t define who are you, but rather says more about the person that’s ghosting — and it’s nothing good! Don’t attempt to mind-read and create a story about why the person is ghosting. Accept that, ultimately, you don’t know why. Tolerating the unknown is difficult in any context — especially when it comes to dating, when you’re excited about someone — but do your best to try to tolerate the uncertainty and ambiguity. Because that’s far preferable, and much healthier, than making up a story about what’s wrong with you.” –Schaffer

On Text Interpretation

Q: “Are there any general rules when it comes to reading the tone of a text? How can you avoid misunderstandings?” –Maya, 25, Manhattan

A: “First rule of thumb: No drunk texting! That’s never a good idea, as you know if you’ve ever done it. Get one of those apps that has safety measures to prevent you from doing so, or, better yet, don’t get so drunk that it’s a regular risk! Secondly: Put off today what you can do tomorrow. Not literally — I don’t mean wait a day to respond to messages to appear mysterious — but in other words, if you’re not sure how you want to respond yet, put down your phone and ruminate for awhile before sending a message. In this digital age, the concept of empathy sometimes gets lost on the screen. In texting, think about what you would like to hear/read via text. Put yourself in the other person’s shoes and think about how s/he would feel reading your text. And sometimes, if there’s a pattern of misunderstandings — some people are better at texting than others — just suggest meeting in person or hopping on the phone to talk about anything important, rather than risking misinterpretation or unnecessary drama.” –Schaffer

On Finances

Q: “How should we split things if my S.O. makes more money than I do? How do we keep it fair?”

A: “Money is harder to talk about than sex. More important than the dollar amount that each partner pays is their intent. I think it’s important to treat each other well. That might mean that the person with the lower income pays for drinks when the higher income partner pays for the pricier dinner. And all offerings should be sincere — so don’t offer to pay just to ‘test’ if someone’s generous or cheap. Honestly offer what you can. For more advice on the subject of money and dating, check out these tips.” –Sommers

MORE: 5 Crucial Dos and Don’ts for Dating a Friend