Name: Anonymous
Age: 27
Location: UK

i am not out as lesbian in work and have had bfs to try and convince myself i wasn’t gay, until out of no where the woman of my dreams started at my work, i knew then, i fell head over heals, she didn’t know obviously, we got on really well, although i got the feeling she was trying to suss me out, she would comment on things about being gay and be watching me while she said them, i don’t know what to think, can she tell, is she playing with me?

shes my boss, i got away with a lot of stuff in work, and the way she looked at me, at my cleavage, 20yrs older, is it even possible for her to look at someone with such a huge age gap, even tho i fell for her. i have left that place now 7mths and i have keep in contact with her, she replies, tho its me that does all the contacting. im playin with the idea of tellin her how i feel because of the fact that i have never fell for someone so quickly and never felt soo strongly about someone, though i might just be seein what i want to see, i know im definitely in love with her, worked with her for a year

Read the TLL Advice Panelists answers after the jump…

Lori Hahn

Dear Anon  -

Now that you’ve left the place, you can certainly risk telling her you’d like to see her.  Infatuation is a very heady thing, after all – and you probably need to resolve this so you can figure out which fork in the road to take.  The fact she never pursues the contact indicates to me it may well be one-sided.  You also fail to mention if she is in any kind of relationship. You probably know since you know her fairly well.   If she’s not – then go for it, but realize a woman that much older might just be flattered by the attention, but really find that they have little in common with someone so much younger – even if she is gay – and she may not be.  If she already in a relationship gay or straight, pursuing a relationship with someone already taken is generally just ill-advised and usually very complicated.  If it were me, I’d start exploring the gay side of life with those in my own age group.  They stay up later than most people pushing 50!

Lori
Hahn at Home

Shanna Katz

Dear Anon -

Your course of action from here on depends.  Are you willing to accept it if she’s not into you (or is in a relationship, or thinks you’re too young, etc)? If so, then I say go for it.  What’s the worst that can happen? And if that isn’t ok, and you want to keep the fantasy of her alive and well in your head, then maybe try finding other queer/gay people with similar interests to your own.

Age is just a number, much of the time. However, twenty years can be more of an issue if you have difference goals/interests. If she wants to settle down and retire, and you want to work all the time, or travel the work, that can cause problems. Make sure you take that into consideration.

Best of luck!

Shanna
www.shannakatz.com

Dharma Kelleher

Dear Anonymous,

Since the two of you are no longer work together, I don’t see any reason not to broach the subject. You might want to try and verify that she is lesbian (or bi) first.

The age gap is significant, but not unheard of. I was a few years older than you are now when my wife and I got together (11 years ago). She’s 15 years older than I am. Keep in mind though that such an age difference brings with it certain challenges. They may come a time when she may not be interested or able to do the things you are interested in doing. You may feel like going to a rock concert while she’d rather stay home and watch the telly. You may end up doing more than half of the housework. That doesn’t mean it can’t work, but it’s important to be aware of such things before getting into a committed relationship.

When you do decide to ask her out, she may not be interested for any number of reasons. If that happens, don’t despair. There are a lot of fish in the sea. Remember, you worth isn’t based on relationship status.

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

Tina-cious

Dear Anon,

I think under the best circumstances one should never tell someone they aren’t dating that they are in love with them.  Seriously, how do you reply to that?  “Ummmm, thanks?”  AWKWARD!

If you no longer work with her and know her to be single or at least are unaware of her relationship status (anything but involved!), I’d ask her out.

What do you have to lose?  Really?  It’s not like she’s your boss anymore… You do risk her not talking to you again but this limbo you are in seems worse to me.

Keep us posted!

Tina-cious

Kelly Leszczynski

Anon,

To me there are very few circumstances where you shouldn’t tell someone you love them. We only get one chance at this life and best to be in love for as much of it as possible. Yes the age difference is a lot, but I assure you that there are harder things that couples have confronted and overcome.

That said I can’t tell you that she will reciprocate. What I can tell you is that you’ll regret it for a long time if you don’t tell her how you feel. The worst thing that can happen is that she tell you she doesn’t feel the same way.

May love give you courage,

Kelly
Brain Clouds

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