Showing someone you are interested in a relationship but not ready to send nude

Question

I'm a male in my early- to mid-20's who has recently connected with a female close to my age by finding her on a dating app. She preferred to have conversations on a separate app, popularly used for sending timed photos, so we added each other on there.

I messaged her and introduced myself; I saw her on the dating app, I attend the same college as her, and I'm interested in a casual relationship (friends with benefits). I offered to meet up with her over food/drinks to get to know each other better. She replied by asking for photos of myself. I obliged by sending a couple normal photos, and one where I was only wearing undergarments. They seemed to have drawn a bit of interest from her, she said I was attractive and she wanted me to take off my undergarments.

I decided not to give her too much too soon by playfully asking if she'd care to send a photo of herself, to which she read but did not respond. She does have some teasing videos and photos (pornographic nature) of herself on her profile, but since I sent her photos first, I wanted to see if she would at least send me something back personally.

As far as online identity and digital footprint type of stuff goes, I'm pretty conscientious about it, so I'm not really willing to put explicit photos of myself out there without some form of reciprocating. She has posted non-explicit photos on her profile recently, so I don't have much reason to believe that it may be a fake profile. I seemed to have piqued her interest and would like to hold on to that, without doing anything that may make her feel like I'm trying to extort her or anything along those lines, while protecting myself as well. I intend to pick up the conversation again, and I'd like to do so without causing undue wariness from either side.

How can I communicate with her that I'd still like to explore this connection, in a way that is mutually beneficial, without making the conversation topic too serious?

Answer 1

Your question is primarily-opinion-based, but I'm just gonna go ahead and say it... Don't share nude or inappropriate pictures of yourself with people you don't know and trust extremely well.

Once they're out there, they're out there, and you can't control where they end up, who they're shared with, etc. They could even come back to haunt you years later, when you're trying to be a professional, or raise a family. (Note the seemingly endless stream of political figures who get caught in scandals because of this sort of thing...)

If you don't know this person well, and they're already asking for nude or inappropriate pictures, without offering to reciprocate there's a fairly reasonable chance that they're not doing it for the reasons you think they are, or would want them to be.

Generally speaking, when people are just being flirtatious and naughty, in good fun, they'll offer photos at some point if that's their thing. You shouldn't really need to ask and asking can come across as presumptuous and/or rude. Always consider that they may not really want naughty pictures, they may have just been playing along.

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Sources... I'd rather not give specifics, but I've done a fair bit of online dating and had third parties show me unsolicited, and jokingly solicited photos. It really does happen.

Answer 2

No precisely on-topic, but important to mention: This situation sounds like a common blackmail scam which preys on dating site users and you could be teetering on the edge of being a victim of catfishing and I advise caution and prudence.

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Whether or not this person is real, asking for nudes before ever meeting is rather forward and unusual. Refusing to do so would be normal, especially with somebody who you have never met in person. Turning down the request, but not shutting down the conversation can be achieved through redirection. Instead of making your response begin and end with turning down the request, transition into moving the flirting and date planning along.

No thanks, you'll have to wait to see me in person for that ;D

When's a good time for you?

Flirtatious text conversations can and should leverage winking emoticons/emoji, as flirting is a playful and semi-serious form of interaction and thats what winking is all about.

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Back to off-topic stuff: This is probably catfishing unfortunately, asking for nudes before ever meeting is a big red flag. Even if they send explicit pictures, you are under no obligation to reciprocate, especially since its really easy to find explicit pictures on the internet and pretend that its you when you want to set people up for some blackmail.