First dates are for testing chemistry, getting to know each other on a very basic level, and generally trying really hard to present oneself as a human being who has their shit together. So real, probing questions are generally off the table. So is any topic that’d be way too serious for even the first few months of casual dating (you probably wouldn’t count « how many kids do you want? » as a first-date icebreaker question). But there are definitely questions guys would love to ask, if it wouldn’t mean totally blowing the first date. Questions that are a little too probing, or might save them some time, or just take the edge off the whole awkwardness of a first date.
1. What is your family actually like? This one likely won’t come into play for a few months, but if things get serious, it’s nice to know who he’ll be dealing with. I’m talking the people that could be related to him through marriage. Is there an uncle who will make uncomfortable sexual innuendos at every holiday? A parent who will mock your career choice no matter how many promotions you get? Is there a black sheep in the family? Are you the black sheep?
2. Why did you actually decide to go out with me? To borrow from Groucho Marx’s famous quote, would you want to date anyone willing to go out with you? Did you feel bad for him and this is just a pity date? Did you think he’s hot? Was it that he makes you laugh? It’s nice to know how he somehow managed to snag this date.
3. Do you have any terrible friends? This might not be a deal breaker, but it’s nice to have a heads up. Sometimes great people have awful friends. At least if he knows in advance, he can plan a defensive strategy in advance.
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4. Are we going to kiss tonight? All right that was too polite: He wants to know if sex is on the table. If you just tell him flat-out, he’ll probably be way less nervous and awkward throughout the date. Probably.
5. How many of your exes did you break up with? This one could be a serious red flag. Either you’ve got terrible taste in guys and don’t realize it until it’s too late, or you get bored of people eventually. Is he really going to be the one to finally break the streak and settle down with you? Probably not. Maybe he’s willing to try, but it’s nice to know the odds in advance.
6. Do you plan on getting certifiably insane several months into this relationship? Some people claim to be « super chill » but then two months into the relationship, wind up freaking out if you don’t text back right away, throwing bottles at you during fights, and showing up to your house unannounced at 5 a.m. « just to check. » It’d be real nice to know when the right time to bail is.
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7. Are you looking for anything serious or do you just want to hook up? This information is crucial. It’s all too easy for a guy to come on too strong because he thinks that’s what you want. Then he scares you off because all you wanted was sex, but that’s also all he wanted anyway. So basically, it’d be nice if there were a polite way to ask you just how hard he should be trying.
8. What’s your sex drive like? The sex always comes fast and intense the first few months. But eventually things settle in. What if you don’t match up? What if he wants to have sex way more (or way less) than you? That can really impact a relationship. It’s just too bad that if he asked this question, you wouldn’t think, Wow! Look at the foresight this guy has! You’d think, This guy is a pervert.
9. How long ago was your last relationship? If you just broke up with your long-term boyfriend yesterday, he’ll probably excuse himself to the bathroom and leave out the window.
10 Are you still in love with your ex? Just tell him politely that he’s a rebound you’ll hook up with a few times before getting back with your ex of five years.
It’s easier for all of us this way.