How Deep Is Too Deep on A First Date?


How deep is too deep

By Ken Solin

Naturally Curious

How deep is it appropriate to dig into someone’s life on a first date? You’re sitting across from your date in a crowded, noisy café that you both agreed was the best venue for this meet and greet. Seniors don’t have a lot of time to lose, and that especially includes wasting time dating someone who doesn’t have viable relationship potential. Seniors want to know as much as possible about how other seniors have spent their lives, because they know these experiences contribute to a relationship.

A Fine Line

Most senior daters have some trepidation about being labeled as nosy or pushy. So how does this fear play out on a first date when we want to learn as much as possible about the other person? It’s tricky, and there’s a fine line between being inquisitive and being over the top. But walking away clueless from a first date is worse than running the risk of offending someone. We want to have a better understanding of who our date is and what are their qualities and values, and without digging in a little, we just can’t know. For that reason, I want to debunk the myth that being nosy or pushy on a first date is a mistake. But having said that, there are areas of your date’s life that are off limits on a first date.


When is the right time to dig deep?

Secrets generally don’t remain hidden for very long in relationships. They get blurted out accidentally, or sometimes on purpose because few seniors have the ability or desire to hide anything substantial from someone they love. With a few exceptions, whatever you want to know about your date is fair game.

Don’t Go There

But there are two areas in particular seniors shouldn’t probe on a first date. Digging for financial information is totally inappropriate on a first date, and so is asking about your date’s sexual history. The former will likely come out soon enough, and the latter is none of your business on a first date or ever for that matter. Remember, you are looking for shared values and perspectives and not a shared bank account.

inappropriate first date questions

Aside from these two issues, there are other topics that are touchy but fair game. You just have to be sensitive and patient enough to figure out the right timing to ask them.

Sexually Active

While it’s okay to ask whether your date is still sexual, that’s the extent of appropriate, first date sex questions. If you’re still a sexual senior it’s reasonable to discover early on if your date is, too. Discovering whether your date is still sexual avoids potential misunderstanding later. Men must limit themselves to this question regarding sex or they’ll be perceived as sexually aggressive. Most seniors feel sex is desirable, but if it’s not, it’s incumbent upon someone who’s no longer sexual to mention this on a first date to prevent uncomfortable situations.

Seeing A Therapist

Therapy is another fair question, and seniors should be careful not to misinterpret their date’s answer. A yes response to therapy is actually the best response because it indicates an interest in self-awareness, personal growth and emotional health. When I dated I considered a woman who’d been in therapy a terrific choice because it suggested she had done her work and addressed her issues. She recognized that there were sides to her that needed to be worked on and did not avoid her problems. This may feel like an awkward question, but the answer is too important not to ask it.

Past Relationship

What did you learn from your last relationship is a thorny question many seniors don’t think to ask. Many of us don’t like to talk about our last relationship, especially on the first date. But truthfully, the answer is relevant, particularly if your date doesn’t take any responsibility for their failed relationships. Everyone has to admit fault in relationships when they’re wrong, and not being willing to is a bad sign for your relationship with this person.

Probe Carefully

You can’t dig to China on a first date, but you can certainly probe beneath the surface. There’s no reason to be surprised by any of the aforementioned issues down the road, and if you have the courage to ask these questions on a first date, you won’t be. If you fail to ask these and other personal questions, with the exception of the two mentioned as off limits, you’ll spin your wheels a lot.

Are you still skeptical about online dating for seniors? Then you should check out OurTime, an online dating site dedicated to singles 50+.

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