How to ask...

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polyshyguy

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I first brought up polyamory to my wife a couple years ago. It's an idea that she intellectually has no problems with, and sometimes finds intriguing. After much deliberation, and yes/no decisions, she has decided that she'd be okay with me looking for an additional partner. And I feel the same about her dating.

There's a person I've pointed out as being interested in me, and vice versa, and my wife has seen her. This woman works at a local retailer. Whenever she's working, I try to go in her check-out line. We've had friendly conversations a couple of times, and what I think is flirting, but I'm not sure. I've always been bad at telling whether someone is interested, and I've had several bad experiences where I thought someone was, and it turns out they were not, even remotely.

She appears to be somewhat of an alternative type, going by the way she looks and dresses, so it's possible she might be open to a lifestyle like poly. My question is, how do I even bring up the possibility of going out? We'll never even get to know each other to know if this might be possible unless I can at least get that far. I have no contact with her outside of her work, so I don't want to make it an awkward situation for her.
 
Hmm... That's a tough one. I think you could just keep talking more and more each time you see her. (That is what I have been known to do.) That way the relationship develops slowly, and without it being obvious that you are interested, before you know what kind of person they are.

Perhaps you could find what she does for fun somehow, then show up?

I think you should keep looking around, though, as this might not work out. Don't put all your eggs in one basket, so to speak.
 
Thanks, Redpepper. That's good advice.

Sometimes I worry so much about the possibilities, when the easiest thing to do is just be natural. Part of the problem is that she doesn't seem to work very often, so I only see her once a week, at most.

I'm also concerned about how notoriously shy I am. I'd been about five years out of college, with only about three dates under my belt, and no relationships, when I met my wife, and she asked me out the first time.

But it's still a good plan to go slow.

I'm not really the kind of person who needs a poly relationship. My wife and I have done fine together for years. But when I feel a special spark, and the situation seems possible, I'd like to at least look into it.
 
Here is my example. I have been nurturing a relationship with a woman for almost a year. She is the caretaker of the building our company rents from her father. She isn't there often, but whenever she is there, I say hi and talk to her a bit. I found out that she goes to a coffee shop I do, and is, in fact, a regular there. We gave each other a smile at first, and that has led to conversations. I really like her and want to be her friend.

Last night I was at the coffee shop with my partners and my son, and she came in. She met them all and we talked a bit. I managed to tell her some of the things I have been wanting to say for a while about my company's relationship with her dad, that I thought might be getting in the way of us being friends. I was glad to share that. We were in a position where she could hear and hopefully trust me, knowing that I really meant what I said. It took time... Next time I see her I'm going to ask if she wants to go for coffee with me.

I know she is a lesbian. My experience with lesbians is that they haven't understood my pansexuality. It is a step I dread, telling her who the men were that she met (although she knows that one is my son's dad). I intend, if we ever get there, to tell her that I have been nervous to tell her, and why, and then tell her about my situation. I haven't invested in that ever happening, but as you say, I will act naturally and take it in my stride.

I have a big need for lesbian community in my life and that is where I would like to invest. I identified as a lesbian for 10 years before dating and marrying a man. I miss the feeling that community offered. We shall see.

I hope you see from this that time and patience are your friends. Shy or not, it will all unfold.
 
Thanks. I'll keep on the slow path I've been on and see what develops. If I feel the mood is right, I'll ask her to do something casual. Until then... *sigh*
 
Argh! This is driving me nuts! I saw her again tonight, working in another area. But I got all shy and avoided eye contact. I tried to smile at her on the way out, but she wasn't looking. Now I feel like she might have misread my looking away as something negative, and maybe I made her feel bad. Too obsessive, I know, but I really hope she didn't take my shyness the wrong way.
 
polyshyguy said:
Argh! This is driving me nuts... I really hope she didn't take my shyness the wrong way.
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Calm down, start breathing... Here is what you do. Buy something you would be interested in that she may like, as well. Before you buy it, simply ask her what she thinks about it.

What kind of retail store is it?
 
polyshyguy said:
A Target.
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Oh, that's awesome! Ask her to help you find something. As you walk to that thing, just have some chit chat. Thank her for helping you. Then ask her what she does when she isn't there. So on and so forth. Say, "If you'd like to do X, I'd like to... blah blah blah... Don't answer now... Since I asked you, I will give you my number (email or whatever)." Then the ball will be in her court.

My thoughts. :)
 
Well, she usually works at the checkout so I don't think they help people find stuff, but if I could catch her at the photo lab where she sometimes is, and I happen to have some photo-related needs with me, that might work. I don't want this to sound like I'm scheming, and if she's shows signs she's not interested, I'll back off right away, but you're right. I'll throw some photos on a thumb drive, and next time I see her at the photo area, I'll try to make some more in-depth chit-chat.
 
polyshyguy said:
She usually works at the checkout. I don't think they help people find stuff, but if I could catch her at the photo lab where she sometimes is, and I happen to have some photo-related needs with me, that might work. I don't want this to sound like I'm scheming, and if she's shows signs she's not interested I'll back off right away, but you're right. I'll throw some photos on a thumb drive, and next time I see her at the photo area, I'll try to make some more in-depth chit-chat.
Click to expand...

Well, the purpose isn't to actually figure out what to buy, but to start the conversation. Really, don't think too much about what to say, but how you say it. Treat her as a friend, and don't put too much expectation on the outcome, just relax. You like her because she is cool and maybe an interesting person, so go with the purpose of seeing if she is as cool and interesting once you talk to her. Ger her email or phone number and then you can start planning the next move.

I get nervous talking to people, especially those I like, but hey, what is really the worst thing that can happen? She would just say "no", no biggie. :)
 
Yeah, honestly I'm only nervous out of habit. I have very little to lose in the scenario. IF we hit it off and IF she's open to the idea, it's a possibility, but it's always a possibility that one or the other of those things won't happen. Since I'm already happy with the person I'm with, I have little pressure.

Thanks for the talk-down, guys. I'll let you know how it turns out.
 
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