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Lesbianing With AE: You’re Her First Female Match, So Do You Meet IRL?

Dear AE,

I met this woman online and we’ve been chatting like every day. We’re so compatible it’s freaky…it’s like everything that’s really important to me is important to her, and everything I’ve never felt comfortable sharing with friends I can tell her and she gets it totally. We spend hours texting back and forth. She sends me sexy pictures. We’re planning to meet up next week but now that I’m going to get to know her in real life I’m starting to have second thoughts. This girl was very open with me in letting me know that she’s only had boyfriends in the past and is starting to explore her bisexual side but she has never been with a woman at all. Due to our connection I think there’s potential, but I’ve heard too many horror stories about women who are just getting their fling on to impress a boyfriend. She’s turned up the flirting telling me everything she wants to do to me when we meet, but I’m worried that once I meet in person I will really start to fall for her, just when she will decide she isn’t available to me. Yet I really want to meet her. Since we started talking she’s been all I think about. What do I do?

– Torn

Dear Torn,

Go. Meet her. Be open to what happens. It’s scary but it could pay off super huge with a new relationship with someone who’s exactly who you wanted.

We’ve all been new lesbians before. We all acquired our first girl on girl experience from somewhere. This woman hasn’t been with another woman yet, but that doesn’t mean that her desire isn’t authentic.

You can either decide for her — that she’s a straight girl sick of creepy men (and with the news lately, who can blame her?) or that she’s a lesbian or bi girl coming into her sexuality later in life (female sexuality is sometimes fluid, and we don’t all figure it out in our teens) — or you can let her decide what she wants and hope that it’s you.

You can either decide for her — that she’s a straight girl sick of creepy men (and with the news lately, who can blame her?) or that she’s a lesbian or bi girl coming into her sexuality later in life (female sexuality is sometimes fluid, and we don’t all figure it out in our teens) — or you can let her decide what she wants and hope that it’s you.

Sure, she has never had sex with a woman before. And you know what, so what?

It can be a super fun thrill to be her first woman, if you two wind up in bed together.

But hey, if hands-on experience matters more than, you know, actually connecting, then sure, hold out for the gold stars you click with.

But you’ve got a real soul connection with this woman. You think about her daily.

There’s more on the line here than there would be with a standard online date where you’re not vibing hard. That’s a good thing. Don’t let your fear get the best of you. You don’t get to find love without a little fear.

Maybe this woman is a new lesbian, or maybe she’s another straight girl trying it on for novelty. Forget her for a second: Who are you? Are you the woman who plays it safe in hopes of avoiding heartache, or are you the woman who shows up even when it’s scary?

Need some advice? Write to us! Send your email to [email protected] with “Ask Jenny” in the subject line!

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