{"id":17906,"date":"2018-12-10T14:00:43","date_gmt":"2018-12-10T22:00:43","guid":{"rendered":"https:\/\/datemixstaging.wpengine.com\/?p=17906"},"modified":"2021-05-31T10:05:38","modified_gmt":"2021-05-31T17:05:38","slug":"awkward-questions","status":"publish","type":"post","link":"https:\/\/www.zoosk.com\/date-mix\/relationship-advice\/awkward-questions\/","title":{"rendered":"60 Awkward Questions to Ask the Person You&#8217;re Dating"},"content":{"rendered":"\n<p><span style=\"font-weight: 400;\">Before you wonder, let\u2019s clear something up. No one <\/span><i><span style=\"font-weight: 400;\">wants<\/span><\/i><span style=\"font-weight: 400;\"> to ask or be asked an awkward question\u2014so why bother? Unfortunately, asking the awkward hard-hitting questions is how people can really get down to the nitty gritty of who they&#8217;re dating and where things are going in the relationship. <\/span><\/p>\n\n\n\n<p><span style=\"font-weight: 400;\">Though awkward questions are nobody\u2019s favorite thing, here are 60 that will help clarify the situation you&#8217;re in and the personality of who you\u2019re dating. <\/span><span style=\"font-weight: 400;\"><br>\n<\/span><span style=\"font-weight: 400;\"><br>\n<\/span><b>The Serious Questions<\/b><span style=\"font-weight: 400;\"><br>\n<\/span><span style=\"font-weight: 400;\">These questions should probably be worked in slowly, but should definitely be discussed eventually. If you&#8217;re passionate about having kids one day or throwing a huge wedding, it&#8217;s better to find out if the person you&#8217;re dating is on the same page. Some subjects are negotiable, but for many, the following awkward questions are potential deal breakers.<\/span><\/p>\n\n\n\n<ol class=\"wp-block-list\"><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Do you want to get married one day? <\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Do you anticipate having a big wedding or small wedding? <\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Is it important for you to have a traditional wedding or would you be open to something like eloping?<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Do you want to have kids one day? <\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">How many kids do you want to have? <\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Where do you want to live?<\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Are you interested in buying a house? <\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">How important is religion to you? <\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">What kind of debt are you in? <\/span><\/li><li style=\"font-weight: 400;\"><span style=\"font-weight: 400;\">Are you happy in your career? <\/span><\/li><\/ol>\n\n\n\n<p><b>The Past, Present, and Future<br>\n<\/b><span style=\"font-weight: 400;\">People are always told to avoid talking about their exes, but that&#8217;s only true to a certain extent. As things start to get more serious between you and the person you&#8217;re dating, it can be helpful to learn more about how your partner views their past dating experiences. <\/span><\/p>\n\n\n\n<ol class=\"wp-block-list\" start=\"11\"><li><span style=\"font-weight: 400;\"> Have you ever been in love with anyone? <\/span><\/li><li><span style=\"font-weight: 400;\"> Have you ever lived with someone before? <\/span><\/li><li><span style=\"font-weight: 400;\"> How long did your longest relationship last? <\/span><\/li><li><span style=\"font-weight: 400;\"> Why did your last relationship end? <\/span><\/li><li><span style=\"font-weight: 400;\"> What matters to you most in a relationship? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you see us together in five years? <\/span><\/li><li><span style=\"font-weight: 400;\"> What are your goals for dating? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you love me? <\/span><\/li><li><span style=\"font-weight: 400;\"> Have you been married before? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you think about marrying me? <\/span><\/li><\/ol>\n\n\n\n<p><b>The Physical<\/b><span style=\"font-weight: 400;\"><br>\n<\/span><span style=\"font-weight: 400;\">It\u2019s really important to maintain an open dialogue when it comes to sex and your sexual health. (Both of your sexual healths!) Some of these questions will naturally come up as you two get to know each other, but it\u2019s important to check back in from time to time to ensure you&#8217;re both happy, healthy, and comfortable with one another. <\/span><\/p>\n\n\n\n<ol class=\"wp-block-list\" start=\"21\"><li><span style=\"font-weight: 400;\"> What kind of birth control do you take\/prefer? <\/span><\/li><li><span style=\"font-weight: 400;\"> How often do you get tested? <\/span><\/li><li><span style=\"font-weight: 400;\"> Have you ever had a sexually transmitted infection or disease? <\/span><\/li><li><span style=\"font-weight: 400;\"> How would you feel if you and I accidentally got pregnant? <\/span><\/li><li><span style=\"font-weight: 400;\"> What makes you feel comfortable in the bedroom? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you feel like you can talk to me about sex? <\/span><\/li><li><span style=\"font-weight: 400;\"> How old were you when you first had sex? <\/span><\/li><li><span style=\"font-weight: 400;\"> Is there anything our physical relationship is lacking? <\/span><\/li><li><span style=\"font-weight: 400;\"> What can I do to make you feel desired? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you watch pornography? <\/span><\/li><\/ol>\n\n\n\n<p><b>Family History<\/b><b><br>\n<\/b><span style=\"font-weight: 400;\">Discussing familial history can be really tough for people, especially if they come from an unconventional family, or one that has experienced grief or suffering. It\u2019s important to learn all that you can about someone\u2019s family history to better support and understand them as a partner. When appropriate, consider asking them the following questions. <\/span><\/p>\n\n\n\n<ol class=\"wp-block-list\" start=\"31\"><li><span style=\"font-weight: 400;\"> Are you close to your mother? <\/span><\/li><li><span style=\"font-weight: 400;\"> Are you close to your father? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you have living grandparents? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you have siblings? Are you close to them? <\/span><\/li><li><span style=\"font-weight: 400;\"> What traditions from growing up are you keen on keeping up? <\/span><\/li><li><span style=\"font-weight: 400;\"> Is there any part of your childhood you\u2019d like to leave behind?<\/span><\/li><li><span style=\"font-weight: 400;\"> Where did you grow up as a child? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you consider your parents\u2019 relationship to be a healthy one? <\/span><\/li><li><span style=\"font-weight: 400;\"> Was anyone in your family an addict?<\/span><\/li><li><span style=\"font-weight: 400;\"> How can I support you in your grief\/processing with your familial relationships? <\/span><\/li><\/ol>\n\n\n\n<p><b>Vices<br>\n<\/b><span style=\"font-weight: 400;\">This is certainly not a first date conversation, but eventually, as things get more serious, it may be worth asking the following questions to learn more about your partner. You will also get to learn more about how you can support your partner through anything they may struggle with in the future. <\/span><\/p>\n\n\n\n<ol class=\"wp-block-list\" start=\"41\"><li><span style=\"font-weight: 400;\"> What is your biggest vice? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you consider yourself addicted to anything? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you drink alcohol? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you smoke cigarettes? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you do drugs?<\/span><\/li><li><span style=\"font-weight: 400;\"> Have you ever done drugs? <\/span><\/li><li><span style=\"font-weight: 400;\"> Have you ever had a DUI? <\/span><\/li><li><span style=\"font-weight: 400;\"> How old were you when you had your first drink? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you vape? <\/span><\/li><li><span style=\"font-weight: 400;\"> What drugs would you consider doing?&nbsp;<\/span><\/li><\/ol>\n\n\n\n<p><b>Beliefs<\/b><b><br>\n<\/b><span style=\"font-weight: 400;\">From religion to daily routine, the word \u201cbelief\u201d can be a major one. When dating someone new, or even after dating someone for a long time, it\u2019s important to figure out where you two land on some of the more important day-to-day aspects of life. Figuring out your partner\u2019s priorities, interests, and values is key, even though it can be a tough conversation. <\/span><\/p>\n\n\n\n<ol class=\"wp-block-list\" start=\"51\"><li><span style=\"font-weight: 400;\"> Do you believe in God? <\/span><\/li><li><span style=\"font-weight: 400;\"> Did you grow up going to church? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you consider yourself a faithful person? <\/span><\/li><li><span style=\"font-weight: 400;\"> How familiar are you with the Bible? <\/span><\/li><li><span style=\"font-weight: 400;\"> Would you raise your children in the church? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you identify with a political party? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you feel comfortable telling me who you voted for in the last election? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you follow local\/national news? <\/span><\/li><li><span style=\"font-weight: 400;\"> Do you believe in [pick the topic you are most passionate about]?<\/span><\/li><li><span style=\"font-weight: 400;\"> Are you registered to vote? <\/span><\/li><\/ol>\n\n\n\n<p><span style=\"font-weight: 400;\">There are so many different ways to ask the above questions. Make them your own and really make sure you&#8217;re in a comfortable and appropriate setting to fire some of these off. Don\u2019t ask someone out on a first date and bring this list along. Work them into your regular conversations while getting to know each other in a lighter, more fun way. Before you two decide to thoroughly commit to one another, make sure some of the bigger value-based questions have been discussed. They can be awkward, but they&#8217;re also extremely important. A healthy relationship is one that can discuss the tough stuff. So don&#8217;t be afraid to get a little awkward.&nbsp;<\/span><\/p>\n","protected":false},"excerpt":{"rendered":"<p>A healthy relationship is one that can discuss the tough stuff. So don&#8217;t be afraid of a little awkwardness.<\/p>\n","protected":false},"author":144,"featured_media":17907,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[894,891],"tags":[],"class_list":["post-17906","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-healthy-relationships","category-relationship-advice"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.0 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>60 Awkward Questions to Ask the Person You&#039;re Dating<\/title>\n<meta name=\"description\" content=\"A healthy relationship is one that can discuss the tough stuff. 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After studying English Literature in school, she has leaned into her degree and is a full-time content writer, social media manager, and freelance contributor to websites like HelloGiggles.com. You can find her on Twitter and Instagram! 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