It's Caller Day and today we're joined by not one but TWO lovely callers! First we're joined by Megan, who has been wrestling with her dating requirements and being labeled a "gold digger" by friends. Are professional and fiscal success too superficial to put in the "needs" column? Next we're joined by Sarah, who's been scratching her head over pre-first-date etiquette. Is it a bad chess move to send a check-in text before the first date, and if so, where's the line between being pursued and simply getting logistical information? Listen on for the Shandy take! Thanks to our sponsors! - Head to https://www.manukora.com/SHANDY or use code SHANDY to get a free pack of honey sticks with your order - a $15 value! - For Hello Tushy, the sale is actually 40% OFF ALL BIDETS through 6/9! (It was just updated after recorded this!) Go to https://www.hellotushy.com/SHANDY and use code SHANDY for a whopping 40% off your purchase! - Go to https://www.squarespace.com/SHANDY and use code SHANDY for 10% off your first website or domain! - Go to https://www.apostrophe.com/SHANDY and use our code SHANDY to get your first visit for only five dollars! Time Stamps: 0:00 - Welcome To Caller Megan! 18:31 - Shandy Speaks 30:08 - Shandy Debrief 36:47 - Welcome To Caller Sarah! 44:19 - Shandy Speaks 54:13 - Shandy Debrief If you have a relationship question, write us at: dearshandy@gmail.com Support Dear Shandy: https://redcircle.com/dear-shandy/donations Subscribe - https://bit.ly/SubscribeDearShandy Listen on iTunes - https://bit.ly/DearShandyiTunes More Dear Shandy Instagram - https://www.instagram.com/dearshandy Facebook - https://fb.me/dearshandy More Sharleen Instagram - https://www.instagram.com/sharleenjoynt Blog - http://www.alltheprettypandas.com More Andy Instagram - https://www.instagram.com/machinelevine Produced by Gabrielle Galon - https://www.instagram.com/gabsamillion Support this podcast at — https://redcircle.com/dear-shandy/donations Learn more about your ad choices. Visit megaphone.fm/adchoices