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Questions to ask when dating a new guy

We talked to the experts, including a former CIA officer, to figure out what answers you need before you get intimate with him—and what the right questions are to see the red flags.

While it would be easy to maintain my professional objectivity, what remains with me that is fodder for this post is how deeply and profoundly the concepts presented touch on my own journey.

Married at 28, with a history of multiple relationships prior, widowed at 40, following a 12 year “paradoxical marriage,” I have been ostensibly single for nearly 16 years, with the exception of a few short term relationships and friends with benefits interactions.

Figure out if he has an ego by, ironically, stroking it. "A normal, humble guy will take compliments graciously, or even be embarrassed.

But someone who is arrogant will use your words as a jumping off point to brag about themselves or their exploits." If he takes every compliment you give him and follows it with a 10-minute speech about how amazing he is, he's probably not the kind of guy you want to sleep with (read: selfish, and potentially selfish in bed)..

to ask both your partner and yourself before you get in bed.

Some are obvious—almost everybody knows to ask about STIs and birth control, and it makes sense to have a conversation about where the relationship is going. For example, how do you ask a guy you've just met whether he's an arrogant jerk who's selfish in bed? But that doesn't mean you can't figure it out with a few less direct questions.And remember: If he's lying about something as trivial as his job (even if it's just to impress you), he's probably lying about other things too.Flattery is everything—when you're trying to out arrogance, Foley says."If he's respectful when talking about an ex-lover, that's a good sign that he'll be respectful of you," he explains.It can be a little awkward to bluntly ask a guy to reveal his relationship history, so lead in to the question with some (inoffensive) info about past relationships.I could chalk it up to fear of loss and re-creating the worst dynamics of my marriage, analysis paralysis about what I did that contributed to some of the dysfunction in that decade plus two, regret and shame about some of my choices, raising my son as a single parent, experimenting with relationship paradigm options, re-inventing myself, busy-ness with life stuff, focusing on career building and at times, truly enjoying being single and now that my son is an adult, making choices that primarily affect only me.I could second guess “If I knew then what I know now,” and beat myself up over all of the shoulda woulda coulda’s and believe me, I have.Despite what movies tell us, there's no hard and fast rule about when you should have sex with your new guy for the first time.Maybe it's five minutes after you meet him, or maybe it's after marriage—no judgment!But if you've just met him, you probably haven't had the chance to see his true colors.The most important to suss out is any anger or control issues, both of which can be problematic even if you never plan on seeing him again.

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