The Hook Up: She rejected me once — should I ask her out again?



So there’s this girl I’ve had a massive crush on. She’s gorgeous, intelligent, ambitious and good-hearted. Every guy at work wants her but no one has ever had the guts to ask her out.

Well, I actually did something about it. I told her that I’ve always thought she was impressive and I asked her out to dinner. Unfortunately, she said no. She said she’s absolutely flattered, but declined because she doesn’t want to lead me on. I took the rejection very well but still expected her to stop talking to me.

However, the next day at work, there was absolutely no weirdness or avoidance. In fact, the conversations between us flowed more easily and more naturally. Months passed and I no longer work with her, but every time we see each other, we have fun talking and catching up.

My problem isn’t the confidence thing. I just want to know if I should try again even after being rejected. Would you advise against it? She never said she was straight. When I first asked her out, I was newly single and I wasn’t in the best place. Maybe she knew that. I’ve grown since then. So should I try again? And what do I say?—Rejected But Hopeful


Dear RBH,

Virtual high-fives to you for being gutsy and going for what you want. That is a hurdle 90 percent of us never get past, so I applaud your efforts and confidence. However, I would advise against straight-up asking this gal out again.

You put yourself out there and she gave you an honest response that she didn’t want to “lead you on.” If her situation had been different that first time, that is, if she had a boyfriend or girlfriend, or she was just recovering from a breakup, it might be different. But that does not appear to be the case here.

Asking her out again, especially now that you’re in a place where you’re friendly and on good terms, is only going to make things awkward, and possibly damage the friendship you’ve built up.

If you want to put out a subtle, flirtatious feeler to see if she might be receptive to taking the olive branch, you can do that, but do it with finesse. For instance, if you’re talking about dating and she bemoans that it’s hard, jokingly say, “Well, my offer of dinner is still valid if you need a change.” Or something else that conveys a casual and noncommittal tone.

The goal is to not make her uncomfortable or to come off as that person who can’t take a hint. If you keep your tone and flirtation light, it should get the point across without overstepping anyone’s boundaries.

Good luck, RBH. And make sure you’re pursuing other ladies. Don’t put all your eggs in one basket, as they say. Put them in several baskets, a tote bag, and a canoe. Just because.


Hi Anna,

You ROCK. Your advice is so on point! And I badly need some.

I was in a relationship for seven months until, all of a sudden, she broke up with me. She said she doesn’t want to be with me because she can’t stand being her family wouldn’t approve and she’s not out to them. I wanted to move on right and to stop all forms of communication with her, but I love her so much that I gave in to what she wanted, which was to keep the communication as is, to still treat each other like “lovers,” and so the only thing that changed was the commitment. That setup lasted for a year!

Eventually she admitted that a lesbian friend was pursuing her, and she said it was time for her to “mingle.” Yes, “mingle” was the term she used. So I said to her that I couldn’t stand seeing and knowing her “mingling” with others so it was better for us to STOP everything. She cried and has been sending me a ton of emails, texts, calling me on the phone, and messaging me on social media.

I broke down and wrote her back a few times, but I don’t know what to do now. I don’t know what to think about her gestures. Should I reply to her?—Bothered and Puzzled


Dear BAP,

The great poet Emily Dickinson (who was queer, did you know that?) once wrote, “After great pain, a formal feeling comes.” Now is the time for you to formally rebuild yourself, to pick up the shards of your heart that have scattered in the wind during this long and tumultuous breakup.

I will be honest with you: It is not joyous work. Recovering yourself after a breakup is exhausting, unrewarding, and painful. But it’s also necessary. And it’s healing.

Because your ex is not terrific about respecting your boundaries, and perhaps because you weren’t 100 percent clear the first (few) times, send her one more message that says, in effect, “I need some time apart from you to deal with this breakup. Don’t contact me for X amount of time (say, 90 days). This is hard on both of us, but I need this space right now, and I need you to respect my decision. I will not reply to any communication until X time has passed.”

If 90 days passes and the thought of seeing her or talking to her makes you want to punch yourself in the stomach, then take more time. It’s not an exact science, matters of the heart.

Judging by her previous actions, she might still try to contact you, and frankly, at that point, I would probably block her from contacting you. I know that sounds harsh, but you are grieving and she is intentionally hurting you and disrespecting your wishes. That is not the kind of person you need in your life during this trying time.

If you find yourself wanting to contact her, employ some of the methods I’ve talked about before here: 5 ways to cultivate willpower. Particularly relevant from that column is the notion of a “sponsor,” like they have in AA, except this sponsor you contact when you really, really want to call your ex.

And don’t forget to lean on your friends. Don’t spend all your time in dark corners alone. Reach out. Ask for help. Mending your heart is fucking brutal, but it’s made less so by surrounding yourself with people who care about you.

As Joss Whedon, the powerhouse behind Buffy the Vampire and other cult faves, once said, “If you can’t run, you crawl. If you can’t crawl—you find someone to carry you.”

Good luck, BAP. The hardest part was making the decision to end things, so you’re on your way.

Anna is a freelance writer in Oakland. Get overly personal emails and haiku from her at Or Twitter @annapulley. Send her your Hook Up questions at [email protected] 

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