Name: Jean

Age: 40′s
Location: CA

I met someone online and we’ve been chatting and Skyping for about three months. We live 3000 miles apart and decided to meet at a resort for a long weekend. We’ve been “flirty” in our chats, but here’s my problem. She’s in the closet, recently divorced, just coming to terms with her sexuality. I would love for something to happen between us, but don’t want to freak her out. Do I take the initiative and plan a romantic evening and make a slow advance? Or do I sit back and let her make the first move?

Read the TLL Advice Panelists answers after the jump…

Lori Hahn

Hi Jean,

Well, I guess if no one was ever willing to be the first, we’d have a lot of sexually frustrated lesbians-in-waiting. But, a word of caution from someone who’s captured more than one toaster oven (is that an incredibly outdated reference now? I’m so old, I never know) – she’s not out, recently divorced, and has children. The children should come first and they hopefully will. She’ll have things that continue to need ironing out with the ex and the sheer emotional magnitude of shifting to a new lifestyle (and I’m talking both as a single mother and potential new lesbian). Her friends and family will have issues. She may not be willing to expose her new found sexuality to her children for some time, which would limit your visits. She’ll probably never out herself at work (for the foreseeable future, at any rate). She’s already laid out the limitations of the potential at this point in time. The closet is a very, very tricky place if you’re not in it.

All that aside, 3,000 miles is a freakin’ long way. Having done long-term, out-of-state dating on more than one occasion, I can tell you it’s always vacation romance and never reality.

But, if she’s just looking for someone to launch her into sexual discovery and you are not looking for more, it may work out great. If that’s the sum of the situation, then I’d say jump in with both feet – make the first move – she’s probably counting on it. I mean, who goes away for a long weekend at a resort with someone they’ve been in contact with for three months? Really. Go for it.

Good luck!

L
Hahn at Home

Shanna Katz

Jean-

Phew~ you’ve got yourself all worked up.  Yes, it is hard to be someone’s first, but remember, EVERYONE has a first as some point (statistically, it’s 100%).  So you’re her first – awesome! Sounds like you’re a very kind and caring person, so lucky her. My suggestion would be to kind of meet a middle ground. Plan things that could be seen as a date/romantic-ish, or could be done between friends, and let her ease into it at her comfort level.  Dinner (not at a candle lit Italian restaurant – I’m talking maybe a burger joint, or the new Thai place that just opened) and a movie. Bowling and ice cream. Things that are not specifically date material, but could be.  She’s nervous – weren’t you with your first? Patience. It’s ok to let her know how you feel, and how much you like her, but let her set the pace.

Good luck!

Shanna
www.shannakatz.com

Dharma Kelleher

Dear Jean,

One of my rules is: Never date anyone in the closet. The guilt, shame and fear will kill the relationship sooner or later, and will take an emotional toll on both of you. And considering she lives 3000 miles away, there isn’t the opportunity for a real relationship anyway. My suggestion would be to be friends only or nothing at all.

I would also suggest you do some introspection and get really honest about what it is about a closeted, physically absent person that is so much more attractive than the openly gay woman closer to home. It could be an indication of wanting to feel loved without wanting the other person to see the real you. Only you can decide what’s true for you, but honesty about this is crucial to finding a healthy, loving and long-lasting relationship.

Love yourself first and trust the process.

Peace out,
Dharma Kelleher
http://www.dharmakelleher.com/

Tina-cious

Dear Freaked,

It’s pretty obvious that she’s interested in you if she’s even entertaining the notion of spending the weekend with you… and, honestly, in my opinion, if she’s going to do that — then she’s expecting SOMETHING to happen — maybe not sex but at least SOMETHING…

I know I wouldn’t fly out somewhere to meet a lesbian for the weekend if I didn’t think we were gonna get down… but hey, that’s just me.

My opinion is that you need to decide ahead of time what you want from this woman.  If she lives 3,000 miles away and has 3 kids and a job she loves — what are the possibilities for a future with her?  Would you be willing to move if things got heavy?

Are you willing to be a step-parent if things go that far?

Are you willing to deal w/ living partially in the closet?

Are you willing to deal w/ an ex-husband who will likely not acknowledge your relationship?

That’s a lot to think about…  if you’re just in it for sex (which is ok by me too) then go do the weekend thing and feel her out — if she’s flirty and seems interested — try to wait for her to make a move — but — if she doesn’t — make a small move and see how that plays out… then go from there.

I’d say don’t go too far overboard in the romantic planning — but definitely bring your A game…

Personally, unless I was just interested in a fling — I wouldn’t go there with this woman.

She’s about to go through a LOT and you aren’t close enough to help her through it.

…my 2 cents…

Tina-cious

Kelly Leszczynski

Jean,

First off, 3000 miles is a whole lot-o-miles! And since long distance relationships are all about communication I would simply talk with her about things. You will have some planning to do the next time you meet so I don’t see anything wrong with talking about whether or not a romantic evening is on the table.

There’s nothing wrong with taking things slow. However if that’s not the route you want to take may I suggest phone sex. Some find it taboo, I find it just the right thing for just the right situation. This may be one of them. If she is comfortable with phone sex then taking the next step may not feel as far of a fall for her.

At this point I think you need to figure out just how much of your heart is in this. Do you love her? Do you love what you feel like you can’t have? Can your love withstand the distance? These are all questions I would ask myself if I were in the same situation.

If anything is worth it, love is!

Kelly
Brain Clouds

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