1. “So, what are you looking for?” - First of all, few people ever answer this honestly. Second of all, many people don’t have an answer for that question. Ask someone if they are looking for a relationship and they are likely to say yes. That doesn’t mean they want one now or with you. They don’t know yet. They’re allowed to not know. As we’ve said before, anybody who leap frogs all the other steps and jumps right in to commitment usually does so for a reason. And that reason is usually that they’re hiding something like a shady past or serious personality/emotional defect. One client told me yesterday that a coach she worked with told her to include her relationships goals – including how she wanted another child and was looking for a long term and committed relationship – in her profile
2.” Who sent you that text?” - Here’s a fun conversation to have at 2am when you and your guy are basking in the afterglow of your sweet, sweet lovin’. I recently had this happen to me, and the five or so minutes after that text bell rang were rather..uncomfortable. There’s no way you can lie about a text coming in after 11pm. We all know what it is. You can ignore it, of course. But then that, too, makes you look guilty. So the only answer you can give in that moment is the truth. Yes, dear. She or he has been with someone else other than you at some point. Side note: turn your phone off.
3. “When was your last relationship?” - I find questions like this funny, because it’s not like the answer is actually going to deter someone from seeing you again. Oh, and because people will probably lie or fudge the truth. Pointless.
4. “Are you dating anyone else?” - If you have to ask then you probably already know the answer. Always assume the answer is yes and base your decisions on that. Asking someone that question puts them on the defensive.It also makes you look all shades of anxious and needy.
5.”How can you be single?/Why are you single?” - Dear God in heaven, don’t ask a single woman this. Especially if she’s over 35. She will plummet down that rabbit hole and land with a resounding thud faster than you can say, “Just curious!” Truth is, you probably don’t want to know why, and no answer is going to reassure you that the person sitting across from you isn’t an emotional cripple or socially awkward shut in. Ideally, you want to know why you’re single. However, you don’t necessarily want to share that fact with some stranger. Don’t turn the question around on the other person. It will make you look defensive. Just say, “I guess because I haven’t met anybody that I’ve been really excited about.”
6. “How many people have you slept with?” – Don’t ask this. Ever. Ever ever ever. If asked, and your number is objectively “high” lie.
7. “Who is that person who posted on your Wall/Tweeted at you?” - You need to wait until you’re in a really comfortable place with someone before you can inquire about things like this. Any time before you’re exclusive or settled in to a consistent pattern of seeing each other will make you look possessive and clingy.
Anyone have any others?