Third dates are a sweet spot. You’ve gone out a few times, you’ve established an obvious rapport and you’re trying to figure out if there’s something special between you. It’s a big turning point in a (potential) relationship and there’s a lot you should know about a guy by then, especially these things.
- When he was last tested for STIs If you haven’t hooked up yet, you probably will soon. Save yourself from the awkwardness of ruining the mood by asking about his STI status NOW rather than mid-makeout, minutes before your clothes are off. Just ask the dude when he was last tested and whether he’s clean before it gets to that point. If he gets all fidgety about it, you should be skeptical. A confident guy who knows he’s STI-free will say as much and won’t be weird about. (That being said, remember it’s always safer to use condoms until you have actual physical proof that he’s actually STI-free!)
- Where he lives You’re not a stalker for wanting this info. In fact, if you don’t know the town or neighborhood he lives in by the end of the first date, I’d be a little freaked. If you guys truly hit it off, you might be spending a lot of your time there…or not. What if he lives in another town or in his parents’ basement? This is important info.
- Whether he wants a relationship or just something casual Never leave the third date wondering whether he’s looking for something serious or if he just wants to hook up. Be direct about it and ask him where he stands on date one so you’re not wasting either of your time. You’re not trying to get married when you’ve just met, but you at least deserve to know if he’s open to a potential future if you really hit it off.
- The scoop on his previous relationship If a dude can’t talk about his ex with you or gets super weird when you bring up a previous relationship then one of two things is going on. Either she’s not completely out of the picture or he’s not completely over their relationship and he’s rebounding hard. Asking doesn’t make you nosy or mean you’re coming on too strong, it just makes you smart and protective of your heart.
- His financial situation Is he really Big Spender Bill or actually Frugal Phil? Some guys will treat you to super lavish dates at the beginning just to impress you even though they’re actually cheapskates. The solution is easy—just ask him how he feels about money, splitting the check, and sharing expenses in a relationship. In my estimation, the third date is a great place to talk about these things. You’re comfortable enough to let your guard down a little bit more but you still have time to execute an exit strategy if you find that you don’t align as well as you thought you did.
- What his sense of humor is like Even if you don’t require a super funny guy, it’s important to know his sense of humor. Is he sarcastic? Does he like dry and dark humor? Is he crude or politically incorrect? Is he kind of corny? Pay attention to the things he thinks are funny and ask him what kind of comedy he enjoys. More importantly, pay attention to how many times you laugh on your date. You might end up spending a lot of time with this dude—he needs to be able to put a smile on your face.
- Whether he has any big obligations Is he recently divorced or does he have children? Is he paying off a huge student loan or does he own a home? I know it can be awkward to get this information from him but these are things you don’t necessarily want to be blindsided by because they’re the types of obligations that might impact your future with him. For example, if he has a child, he might not be able to spend as much time with you as you’d like. Or, if he owns a home, he might be seeking to plant roots and not move anytime soon. Know what big obligations you need information about and ask him before you get in too deep.
- What his work schedule is like/his career ambitions are Does he have a super busy career or is it flexible? For many women, it’s hard to find someone who is compatible with our own careers and ambitions. It always sucks to hit it off with a guy you might never see because you both have nuts schedules. By the third date, you should know if you’re going to have to compete with his career for his attention, stress yourself out trying to balance yours and his, or if he’s willing to work with you to find a solution because he wants to keep seeing you.
- How many women he’s dated before you OK, I know this sounds silly, but here’s why you want to know. If he’s a serial dater or serial monogamist he might be the type to lead you on for a long time before splitting and finding someone new. On the flip side, if he’s never really dated a woman before and has only had situationships or hookups, he might be super immature and green to the whole love, romance, and dating thing. Both could be red flags in their own right, but knowing this will help you set realistic expectations for the pace of your relationship and guard your heart.