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The Hook Up: Work crushes and starting over

I’m in my late 30s and have spent many years in denial about my feelings for women. While I am still attracted to men there are some women in particular who have always caught my eye. However due to my insecurities and fear, it has always made me stop short. Things changed when I started my new job. I noticed this one woman who stood out immediately, probably because at first glance I thought she was a cute young guy (she’s in her mid-20s). I would peek over at her from a distance whenever she passed by and she’d catch me every time. So one day she gives me a small tentative smile and I froze, then looked away. The physical attraction was instant and my heart was beating fast. I’m sure I was blushing because she gave me another small smile. Again I fumbled by answering quickly and going back to my work.

The problems is because I screwed her two attempts she kinda ignores me and when I try to engage her in any sort of small talk she’s just polite but not really friendly. I get why she’s acting this way because we’re both from the same Caribbean background where homophobia is rampant. She took a step and I did exactly what she was afraid of. So any advice on what to do or is my situation hopeless?-Shy Bi Chick

Anna says: I think so, yes! Now where did I put it-this post-it just says “Jason Priestley” and “buy Nutella” which always solves 90 percent of my problems, but probably doesn’t apply to your situation.

As to whether I’d apply the “hopeless” label to your foxy work crush, I can’t say because all I’ve got to go on is a few shy smiles and a little polite-but-not-overly-friendly small talk. Instead of parsing every detail and sidelong glance and lingering pause over the copy machine, I’d recommend you skip all that bullshit and ask her out to lunch. Don’t make it a date-y request. Make it casual. It’s just lunch, as that dating site is always telling me in emails I never signed up for. If that lunch goes well, ask her for coffee. Do this five to seven times, or however long it takes for you to learn things about her.

You know you’re attracted to her and that she’s Caribbean, which is a start, but just because she dresses in a masculine way doesn’t mean she likes to rug wrestle with the ladies. I mean, I hope she does, but we can’t say for sure. So go on, get to know her. Find out if you’re compatible, if you laugh at the same dry, British humor or enjoy the minor works of Macklemore. Allow yourself to be vulnerable. I know it’s terrifying, but it’s the only way to live. “If it doesn’t challenge you, it doesn’t change you,” as Fred Devito once said. He was probably talking about sit-ups, but whatever.

And congrats on your coming out. You’ve got some wild and exciting times ahead, so you might as well start as soon as possible, don’t you think? Let us know how it works out. Go team!

Three years ago my girlfriend and I broke up, after a year and a half together, and since then she’s been happily taken (which for some reason I’m so jealous of even though I’m happy for her and I hate that I am). I, on the other hand, was seeing a girl in secret (she wasn’t out), but after the Christmas holidays it just suddenly stopped or never started again and she started seeing my other friend (in secret) until it all came out and I was pretty hurt, but didn’t let it show.

In my last year of uni, I fell for my good friend who was straight and had a boyfriend. However, she tried to kiss me when she was drunk off her face but I was relatively sober so said no. Next time I was just as drunk and we did (but she never mentioned it) and twice I woke up in her bed both of us topless with no memory (bloody alcohol!). On our hockey tour we both got super drunk and we left the party to go back to the tent but she wouldn’t go in and just started hugging me and telling me “This is so unfair.” We got into the tent and she starts kissing me and this goes on for a while until we fall asleep spooning. In the morning I’m hungover but remember everything and she wakes up and says she has no recollection of last night.

It’s been a couple of months now and we’ve all left uni. She’s going traveling and I’ve moved away, so is there in any point in ever asking her if she remembers? Finally, with all these events my self-esteem is on the floor and I’ve just moved to Chicago so need to make all new friends and want to meet gay people. I just don’t know how to meet gay people and when your confidence is low it’s so hard to throw yourself in the deep end. What do I do? Thanks in advance!

Anna says: Stop getting black-out drunk with your horny, “straight,” taken friends?

OK, well, I am 99 percent sure that your lusty lush of a friend remembers damn well what happened, especially because it happened multiple times. She might not remember minute details, like the finer points of your discussion about beer pong or precisely how the topless spooning started, but she definitely remembers wanting to put her tongue in your mouth, etc. It’s a convenient excuse for her, especially because she has a boyfriend, to not remember these dalliances because it absolves her from feeling guilty about cheating on him and generally messing with your head.

If you do talk to her, it shouldn’t be to ask her if she has any memory of your multiple make-outs, it should be to ask her to take accountability for them. She’s supposed to be your friend, right? But since you’ve gotten really good at pretending like everything is supergreatthanks, she probably doesn’t know that her actions have actually caused you pain. And I think she should know it. Now, if you want to just blow it off or if the friendship isn’t that important to you, then you might not need to process. But it’s been a few months now and is still bothering you, so it might be a good idea to bring it up with her. If she plays the “I was soooo drunk; what’s gravity? I don’t know!” card, then well, at least you tried to be honest about what transpired between you and how it affected you. Which I think you should start doing more, as a general rule.

The way to pick your self-esteem up off the floor is to stop letting people use you as their doormat. You have feelings, I trust? You’re a ghey ladee, so you probably have at least 37 occurring at any given moment. Express them. It’s okay to tell people that they’ve upset you. And vice versa. It doesn’t make you a terrible person. It just makes you a person.

Also, Chicago! You will have so much fun there. I basically came out in Chicago and it’s a very welcoming and adaptive city. I met my gay posse on the sidewalk outside of T’s (R.I.P. T’s!) during Pride weekend-I just said, “Happy Pride!” It was that easy. We were all just stoked to be gay. Grab a wingman (not one who is only gay while intoxicated!) and go to some gay events. FKA and Chances are both really fun. But do be wary of drink specials at gay bars. No one goes to Spin without throwing up at least once.

If you’re less keen on the booze scene, then check out Genderqueer Chicago or any other number of queer-friendly groups out there. Shoot, I’ll even give you the numbers of all my exes in Chicago since you’re bound to date them anyway. But whatever you do, don’t let two less than stellar experiences with not-out ladies impinge on your life’s new direction. I think you’ll find it’s fairly easy to make gay friends. Start from there if you’re wary of dating just yet.

And maybe take up a few more sober activities while you’re at it. I’d recommend Cards Against Humanity and obsessively categorizing potential dates on OkCupid. Or yoga. Yoga is good.

Best of luck!

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at annapulley.com and on Twitter @annapulley. Send her your The Hook Up questions at [email protected].

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