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The original was posted on /r/bestofredditorupdates by /u/Direct-Caterpillar77 on 2026-08-19 04:02:02+00:00.

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I am not The OOP, OOP is u/embarrassedtosend

Me [30F] with my BF [30M] duration, I want to send him sexy pictures as a surprise but I don't know if I should.

Original Post  Sept 20, 2016

I know this issue seems really minor, especially compared to other people's problems but I'd really appreciate any advice. I'm sorry if this seems all over the place, I'm just really embarrassed right now, haha...

My boyfriend and I have been together for nearly two years now and it's been great! We make time for each other, we respect each other's privacy when the other needs it, we always keep in contact and we always do our best to resolve any issues that erupt. Most of all, he respects my feelings on a certain matter, and always has.

I have really bad self-confidence, I guess. I don't like photos being taken of me and I had how my body looks. I know I'm overweight, but not terribly so, but I still get really embarrassed if anyone takes a photo of me, or even if I take a photo of myself. Ben has only one photo of me from the two years we've been together. I said yes to the one, but then I freaked out about how badly I looked that I almost cried. Ben assured me that it was a really good photo, and even though, I was hesitant, I let him keep it. Ever since then, he hasn't asked for any other pictures of me. He's been very patient about how I feel about photo taking. I've been trying to get over this issue of self-confidence, but it's been tough. I have been actively trying to lose weight though, so it's helped a little there. I've even forced myself to take some pictures of my face and I did...but I still deleted them right after.

These past few weeks, Ben has been on a business trip out of the country and I miss him terribly. We still talk to each other every day, but it's not the same with him so far away. I wanted to surprise him and went out and bought some really nice sexy lingerie, and tbh...it's the first time I've ever bought any of this stuff. I've always hated how I looked in them, and was really embarrassed to try them on, but I found some stuff I really liked and I feel like I don't look completely terrible in them and decided to pick it up.

I sent Ben a message saying how I can't wait for him to come back in a few days, because I have a surprise for him. He's been trying to guess what it is since then, but he doesn't have a clue, lol. While he was guessing, I started entertaining the idea that it might be fun to send him a few pictures to get him excited. And even though it's a HUGE step for me, I kinda want to try it for Ben. Because he's respected my feelings all this time, and has always been there for me when I've needed him and most of all, it's Ben and I know I can trust him.

But I don't know if Ben would even want pictures like me in lingerie. He's never asked for them. I'm worried if I send some he won't like them or might even get offended. But if I ask, I feel like I'm ruining a fun surprise that I'm hoping goes well.

So I guess I'm asking: Do you think this is a good idea?
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  tl;dr: Bad confidence issues means I never really take pictures of my face, let alone my body. Boyfriend has always respected that and while he's been away on a business trip I bought my first sets of lingerie and decided to try to take the plunge and send him pictures as a surprise. Don't know how he'll react, though so I'm second-guessing myself.

RELEVANT COMMENTS

AllegedlyNorah

He hasn't asked for any sexy pics for the same reason he hasn't bothered you about any pictures at all. You've explicitly told him you don't like to take photos! Why would he ask you for sexy lingerie pics if you can't even stand him having a picture of you fully clothed? As you said, he's respecting your feelings.

Take the pic and send it to him. It'll be a nice surprise and he'll love it because he loves you.

OOP

I think that's why I suddenly had this idea to send him these photos. Respecting my feelings on the subject says so much to me about him as a person that out of anyone in the world, he's the only person I'd ever consider doing this for. I love him very much and you reminded me so much of why.

~

Snuffleupagus03

Send them.  I get it's hard for you but:

1. he will react positively and love them
2. it's a great step in your self confidence
3. if he doesn't react positively it's not a good sign about him or the relationship (and everything you say about him says this won't happen).

What a great surprise.  He'll be thrilled.

OOP

Well, I hope he likes it, I really only want him to be happy because he's brought me so much joy since I've met him, even in our hardest times, we've worked through them and never said anything we'd regret.

I think I will send them. I want to show him how much I care for him.

~

[deleted]

If you are 100% comfortable about it, you should definitely go for it!

He sounds very patient, understanding and respectful of you which is always great. He will love them!

If it makes you feel more comfortable, only focus on one part of your body in the photo (ex. Boobs or ass in the lingerie). It's a nice little tease for him and is less intimidating than a full body shot (and also I know a lot of people are uncomfortable with leaving their face in explicit photos anyways).

Goodluck! Don't pressure yourself on getting the "perfect" photo, he'll appreciate it!

OOP

I'm still not 100% comfortable with even just taking my picture, but I feel like this will definitely make me feel better about myself, and I do want to show him how much I love him and trust him.

Thank you for the tip about focusing on one part of my body for the photo. :)

Update  Sept 28, 2016 (8 days later)

I just want to thank everyone who commented on my previous post. This issue is such a non-issue that I can't believe how seriously you all took me. All the tips, caution, the encouragement just reminded me how wonderful everyone here can be.

Thanks to you guys and the post I made, I was reminded of all the wonderful qualities and reasons I fell in love with my boyfriend and I decided to send him some pictures. It took awhile to find one I felt comfortable with, but I did find one! I know some people think I shouldn't, but I did include my face in it because I feel like it helped show how much I trust Ben and how much I love him.

I waited until the late evening when he told me how he was getting ready for head off to bed when I messaged him with a picture and then sent "More surprises when you get back ;)" and I'll admit, I got a little panicky. After a few minutes, Ben sent a message back with "Oooh very sexy! <3" and pretty much that was that (Outside of our usual goodnights and I love yous).

I'll admit it, reddit, I didn't know how to take his message back on account of having never sent a photo like this before. Was he being nice? Was this a typical response which was good? Should he have said more? Should I have said more? I didn't know how to feel other than a little disappointed, especially with how long it took me to take the photo. Alongside this, Ben sent me a message the next day telling me about how busy he'll be and then never responded back. I got upset and started feeling like I made a mistake. I spent my day off work with a mix of disappointment, regret and panic, a panic that I had made a huge mistake.

Well, that afternoon I got a knock at my door and who was there? Ben. That's who was at my door. Ben and a bunch of flowers. I wasn't expecting him for a few more days and before I could say anything he told me about how he pulled a favor with his boss (whom he's friendly with) and because the team had pretty much finished up their project he got the go ahead to head home early. Ben told me that he saw the picture and was speechless for a few minutes because he had never expected anything like that from me but knew he had to get home right away to see me. And then he said he felt like the luckiest man in the world.

We've spent every day together since and we've had a fabulous time and I've never felt better about my relationship and about myself. Ben has already asked if he'll get another picture anytime soon. I told him "Only if you're good" :)

tl;dr: Sent picture, discovered I now need to get a full wardrobe of sexy lingerie. I feel great!

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