Dos and Don’ts of Online Dating Questions

Some of you might scan this list and think, What?! Who does that? Well, I’m here to tell you that plenty of guys do. In my many years as an online dater, I’ve seen all these messaging mistakes, and worse!

Yes, it can be nerve-wracking to come up with something that will grab her attention and make her want to write back, but it seems like lots of guys when faced with the task say fuck it and send out whatever crazy shit that pops into their heads. Here are some suggestions to help stop the madness.

Do Ask Her What She Enjoys Doing in Her Spare Time

This is a very casual, nonthreatening thing to ask. If she responds with something flirty like, “Chatting with hotties online,” you know she’s open to being a bit playful. If she answers with something more neutral, you can still propel the conversation forward by asking for more details, or pointing out the things you have in common.

It’s important to find a jumping off point in your initial message that won’t get her back up, or make her feel that you’re desperate to get laid.

Don’t Ask Her “What’s Up?”

Or “Sup?” or “How’s your day going?” I realize these questions sound harmless and friendly, which is probably why so many guys ask these, but they’re also boring, dead-end questions that make her do all the work. How do you tell a total stranger “what’s up” without getting way too personal?

Usually she’ll just say, “Nothing much” and leave it at that. If she gives you any more than that, you know she’s somewhat interested. Even so, be ready to ask more questions that will make it easier for her to open up.

Do Ask Her Something Related to Her Profile

This shows a) that you’ve actually read it, and b) that you’re interested in her for more reasons than just her appearance. Sticking to topics she’s raised in her profile is also a way of avoiding topics that might be off-limits to her. If she’s put it in her bio, you know she’s comfortable talking about it.

Pay special attention to the tone of her profile too. Is she reserved? Open? Professional sounding? Does she talk about her sexual likes and dislikes? If so, it might be okay to ask her more questions to that end. Just don’t try to make the whole conversation revolve around sex.

Don’t Ask Her if She Likes Dick

Any time I’m asked this question by a guy I barely know, it makes me throw up in my mouth a little. It also makes me want to swear off dicks—and the men attached to them—for life.

The only time it’s appropriate for you to ask this question is if you’re about to have sex and want to make sure she’s down with it. Even then, you might want to phrase things differently, like “Do you want to have sex?”

Do Ask Her Out on a Date

Don’t let the conversation drag on for too long before suggesting that you meet in person. Feel it out. If she seems a bit shy or nervous, don’t rush things, but be mindful that if the conversation is going well, she’ll probably want to meet you.

If this seems too forward, ask for her number. You can text for a bit, but also don’t be afraid to call. Lots of women like it when a guy takes initiative, just do so in a respectful, no-pressure way.

Don’t Ask Her to Show You Her Boobs

If she wants to show you her boobs, you won’t have to ask. She’ll do it when, or if, she feels inspired to. If you make a good enough impression and don’t pressure her into anything, you’ll probably get to see them in person, sooner than later.

On the flip side, don’t send a dick pic, or whip it out over Skype unless she’s asked you to. If she hasn’t asked, you can assume it’s not something she’s interested in seeing.

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