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?

  • We can't decide for you what is appropriate, or reasonable. We can help you understand how to ask and communicate to this woman about what is expected between you both. Can you re-word the question to focus on this interpersonal exchange, and we try to focus on just one question at a time, so can you narrow down your question to one thing? Perhaps it'd be better to focus on "If I decided to pick up the conversation again..." - We can't decide for you whether to do so, but we can help you with methods to communicate clearly before sending each other any photos.
    – ElizB
    Nov 5, 2018 at 1:50
  • Thanks for the feedback, I will try and revise my question. I did not mean for this question to come across as "what should I do". I do intend to pick up the conversation again, and I'm interesting in doing so without coming across the wrong way. Clearly, I don't have much experience in these kinds of interactions, so I'm looking to learn about what may be considered "common courtesies" in these exchanges. Nov 5, 2018 at 7:04
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    You say she goes to the same college as you, and that you have offered to meet in person, but have you actually met her in person yet?
    – user8671
    Nov 5, 2018 at 8:47
  • @Kozaky No, we haven't met in person yet. What is described in the OP is the extent of our conversations. Nov 5, 2018 at 9:20
  • You do not state where you are; social norms differ by location or by culture. Perhaps you can state your location, or background or give some idea of hers if you know it. Nov 5, 2018 at 11:27

2 Answers 2


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.

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.

  • This is something I probably could have made clearer in my post; by "teasing videos and photos", I meant pornographic content. It's clear to me that this type of exchange is her "thing". I suppose what I'm wondering is, since she has already put these out on her profile, is asking for more to reciprocate on my photo sharing considered too much to ask? Perhaps she feels like she's already put herself out there enough, so I'm the one that should be reciprocating? I'm not using this as an excuse to disregard the solid advice from both of you, just thought it might be a necessary clarification. Nov 5, 2018 at 10:04
  • While worth stating, this answer doesn't address the re-opened version of the question Nov 13, 2018 at 1:25
  • @spiralsucculent appears to have been a pretty radical edit.
    – apaul
    Nov 13, 2018 at 1:41
  • yep, sorry, I phrased that nicer the second time i posted it on Astralbee's answer Nov 13, 2018 at 1:42

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.

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.

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.

  • 2
    Google reverse image search can be helpful in these cases.
    – apaul
    Nov 13, 2018 at 2:01

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