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Friend I May Start Dating

Started by girlinguyjeans, June 08, 2014, 04:03:44 PM

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girlinguyjeans

So, first I want to say sorry for disappearing off of Susan's for so long (sorry!), I've been pretty busy with work and all lately, but I'm still here! Anyways, I have this friend at work and she's always seemed pretty special to me. She started working at my job a few weeks after I broke up with my girlfriend of two years and we quickly became friends, despite the fact I was in a bad place. A few months later I realize just how much of a connection this girl and I have and so I asked her out, she got super excited and said yes and everything was awesome until that night she called and said she couldn't do it as she was going through some stuff of her own, and we agreed to just be friends. That was three months ago. Now we're really trying to just be friends again but it's pretty obvious we still both care for the other more than friends would, and I figured I would ask her out again, seeing as she's hopefully had time to sort through her personal stuff and she still acts like she's interested. However, I don't want to start dating someone and possibly enter a relationship with someone who doesn't know me as my true self; the woman inside. So I figured I'd need to tell her I'm a transsexual woman who's pre-everything and still living as a man. I know this shouldn't upset her too much, as she's openly supportive of trans people and is pretty open about being bisexual, but I'm still pretty nervous and want to know how to do it. Should I wait and see if we do start dating and tell her then before things get too serious? Should I just straight up tell her asap? I really have no idea :O
We all build masks to hide behind, for we've all stepped into the bright world without those shells only to be broken and ridiculed. I'm tired of peering at the vast, beautiful but deadly world through these eye holes. I am taking off my mask, whatever may come.
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LordKAT

I think waiting to see how things go after a date or two would be best. But that is me.
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girlinguyjeans

Thanks, LordKAT. I'll probably end up doing that although I get upset when people use my birth name, not too big of a deal though, lol. If things do all go well, how should I say it? Face to face, or written in a text or email or something?
We all build masks to hide behind, for we've all stepped into the bright world without those shells only to be broken and ridiculed. I'm tired of peering at the vast, beautiful but deadly world through these eye holes. I am taking off my mask, whatever may come.
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LordKAT

If things are going well, a simple comment in a public place, face to face, would likely work out quite well.
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girlinguyjeans

Okay thanks! As I stated before I think she'd take it pretty well, although initially it may be a surprise. Well I guess I just need to see what happens after a few dates (assuming she does want to go out with me).
We all build masks to hide behind, for we've all stepped into the bright world without those shells only to be broken and ridiculed. I'm tired of peering at the vast, beautiful but deadly world through these eye holes. I am taking off my mask, whatever may come.
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muffinpants

If it was me, I'd say since y'all are already friends, you could come out to her whenever. It seems like you both are interested and maybe it would help to build your relationship into something closer and more special? Especially since she said she had some problems of her own- I know you said it's been around 3 months and she is acting interested... but maybe if you open up, she will open up as well, perhaps y'all could both help each other out! It sounds exciting, and I hope it goes well!! Good luck!
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girlinguyjeans

@muffinpants that's a great idea. I've thought of it before but I already asked her out (over text because I'm really shy and she's at work). But I suppose because she's open minded and we have chemistry I could just bring it up whenever like you said and it may make us closer, like you said :)

EDIT: I asked her, I'm just waiting for a reply.
We all build masks to hide behind, for we've all stepped into the bright world without those shells only to be broken and ridiculed. I'm tired of peering at the vast, beautiful but deadly world through these eye holes. I am taking off my mask, whatever may come.
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