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elllisaurus

Okay okay, hear me out. 

I have been talking to a few pen-pals and things have been going great. With each pal I've created a great bond and one of them is like an older brother to me I can always come to and ask for advice. We go so well together!

However, my other pen-pals, they're a different story.

Both sent me a letter that they intend to be in a romantic relationship with me. One did after a while of writing (and I do like him a lot too, he's getting out soon and I'm interested for sure) but the other was pretty up front straight away. He said "When I get out I'm gonna make you my Queen", like come on can you be more obvious? The thing is, I told him that I wasn't interested romantically yet he still tried to hit on me. I don't know what to do. He's so nice and he sends me drawings, like outside of the hitting on me he really is a great guy and I'd love to be friends. However I don't want to break his heart. I'm really interested in that other guy I mentioned above, and with his release date getting close, dating him actually seems like a viable option. 

What do I do? Do I tell the soon to be paroled guy about this? Do I double down to the other that we really can't be more than friends? I don't want to lose any of my pen-pals but I also don't want them to think I'm being disingenuous. 

 
Luloo

@Ellisaurus I've been there!... and I agree with @Mjuran, only you, know how much what he says is a fantasy he dreams about or how much he's not respecting your boundaries.
And honestly, sometimes the best way is being blunt - I don't mean rude - but not playing around (if you think his feelings are real). Because being vague could make him think there's hope and from what I read, you're interested in another person and he doesn't have any chance.
Have you already told him you are only friends and his attention makes you feel unconfortable? If you do, and he still hits on you... I'd think about your "friendship". And I'd think about... would you accept someone who keeps hitting on you on the outside, even if you made it clear it's a no?
Hope you can make it work... and good luck with dating the other guy! :)

 
Jeanne555

@Ellisaurus, I think you need to establish your boundaries once again with the guy you consider friends. You can start signing off your letters "Your friend", or tell that guy "you are spoiling me with your drawings, you are such a good friend". Keep mentioning that you guys are friends so that he won't think something else. If he is hitting on you, maybe best course of action would be to say "oh you want to make me a queen? I'd prefer to be your friend". No need to tell the guy you are interested in that there is another penpal that wants to be with you. Especially if you consider the other one to be just a friend. Otherwise this might cause jealousy.
Good luck.

 
mjuran

 I wonder to what degree the pen pal who hits on you is really hitting on you in a way that doesn't respect your feelings about it,  i.e., not listening to you telling him to stop, or to what extent he is merely being flirtatious and playful.  You know best, becasue you've read him, and I have only the one example you've given here to go on.  I would say that if he's doing something that actively makes you worried or uncomfortable, and you've been clear with him you're not at the point of feeling reciprocal, that's something to address with him directly, saying, "This is making me feel a little weird" or whatever you want to say about it.

But possibly he's just being playful and indulging in a little fantasy.  If you're open to it, great, and if you're not, best to be very clear about it. That is the best way to avoid breaking someone's heart, being straight up about the level and type of interest you have in them, when they hint (or boldly state) their interest in you.

I would also regard with skepticism anyone who says he wants to make you his queen shortly after starting to write to you...not that it is necessarily insincere, but it seems a little fantasy-bound, which in a prison environment is pretty understandable.  I think people can be disappointed, but not heartbroken, to have theiri expectations adjusted at an early stage like this.  If you've already tried to adjust his expectations and he's not listening to you...red flag!  His potential heartbreak in that case need not be your concern, because it wasn't of your making.  The best you can do is listen to what you yourself want, or feel, and then be as straightforward with both of your penpals as they are with you, about what they want and feel.