Posted by Ask a Manager
https://www.askamanager.org/2025/11/i-cant-shake-my-crush-on-a-former-coworker-using-vacation-time-at-a-new-job-and-more.html
https://www.askamanager.org/?p=34106
It’s five answers to five questions. Here we go…
1. I can’t shake my crush on a former coworker
I try not to view my coworkers as romantic prospects for the obvious reasons (women come to work to advance their careers, not to cater to the romantic whims of their coworkers!). As a woman in my 20s, I’ve experienced a few sexual overtures at work and in public, and I certainly don’t want to impose my own romantic demands on a fellow young woman who simply wants to do her job.
However, I can’t shake my crush on a former coworker, “Diana.” Over the summer, I worked seasonally on the same large team as Diana. (She does year-round, part-time work for this employer.) While we didn’t always have close interactions during the workday, I loved speaking to her whenever we had the chance to collaborate. She asked me genuine, complex questions about my background and experiences, and she occasionally complimented my appearance and overall demeanor. She has an easygoing, natural charisma and the warmest, most expressive smile I’ve ever seen.
My job ended about six weeks ago, and I considered exchanging phone numbers on my final day of work. (I even spent two weeks rehearsing a low-pressure, work-appropriate script!) However, I decided to restrain the impulse to stay in contact, since I’m uncertain that she even dates women. Also, I purposefully only mentioned my male exes when the workplace discussion turned to comedic date stories. It was clear I loved collaborating with Diana, and I didn’t want her to perceive my good mood as an unwelcome overture from the workplace lesbian. However, I still can’t seem to get over her, and I’m even inclined to return to my former workplace and casually try to exchange phone numbers. (While it’s technically open to the public, this still feels like an overstep.) Can you reassure me I made the work-appropriate choice? I can’t locate her on social media, so I’ll probably have to let her remain a fond memory.
Would you be interested in a friendship with Diana even if you knew for sure she wasn’t interested in anything more? If so, given that you appeared to have a warm, friendly rapport while you worked together and it sounds like you both connected at least a bit, I don’t think it’s inappropriate to stop by and ask if she’d ever want to get coffee.
I would not suggest this if your interest was primarily based on physical attraction, but it sounds like it’s based on the actual conversations you had and that she shared an interest in talking with you, not just “I find you attractive and thus am projecting my own interest on to you” — which is where a lot of these things go wrong.
2. My new coworker is doing too much of my job
I have a new coworker, Dana, who is extremely thorough in her responses to my questions, to the point where she basically does my work for me. It’s a tricky situation in that she is taking over my role as department head as I transition into a new one, but for continuity, I’m maintaining management on a few projects we’re in the middle of. I’m asking her questions out of respect not need — meaning that I don’t actually need her to help me with it but, because ultimately the department now belongs to her, I’m asking for her opinion to honor that new relationship. (The projects live her in department and she’ll be accountable for their implementation once my transition is final).
I was particularly annoyed at her thoroughness recently and was short with her on a call. A few days later, I apologized and explained myself, expressing that her thoroughness is hitting a chord with me due to my own insecurities and it’s something I’m working on. Well, fast forward a couple of weeks later and she is as thorough as ever (basically writing what I should send a client word-for-word after I ask a simple question).
On the one hand, she’s making my job easy by doing it for me. On the other, it really irks me and I’m not sure how to handle this. It is, very much, MY problem – bringing up my own insecurities. And, at the same time, it feels very controlling. (Again, maybe that’s my insecurity?) I like Dana and want to have a positive working relationship with her, so it feels weird to not say something. At the same time, I’m not sure if this is just a sensitivity I need to work on in my own self.
This would be a lot easier if you weren’t continuing to manage those remaining projects, because that’s preventing Dana from fully moving into her job and preventing you from fully moving out of it.
But since that’s the set up, you have two options: (1) you can stop asking her things that you don’t actually need to ask her and instead can just fully manage the projects that are still on your plate and keep her informed rather than consulting her for input. That sounds like it might solve a lot of this. Or (2), you can drop your end of the rope and work on not caring about how much she’s involving herself. It’s sounds like she’s trying to take full ownership of her new job, which isn’t that weird, and it just happens to be rubbing you the wrong way … but if that accounts for most of it and it’s not actually causing work problems, deciding not to care (as much as possible, anyway) might be the way to go.
I would definitely not raise your own insecurities with her again, though; that feels like too much info and emotional burden to put on her when she’s just trying to do her job, and it’s not necessarily actionable on her side anyway. If her actions are causing work problems (duplicating efforts, muddying divisions of labor, etc.), you can raise those specific problems — but if it’s really just about how it’s making you feel, that’s not a conversation to have with her. (It would be different if you were remaining in your current role and this was going to be a long-term issue, but it sounds like it’s short-term and then you’ll fully transition out of the job.)
3. Someone wants to pick my brain — should I ask for a job?
A contact at work reached out to see if they could pass along my name for an information interview. For context, the interviewers are building out a new capacity on their team and they’re looking for advice. I’ve been looking for a new job, so I instantly thought, “Are they open to hiring instead?”
Should I mention this to the intermediate party? Or do I bring it up with the interviewers once we meet? Would that come across as deceptive?
It’s not deceptive. They’re asking for your help; there’s nothing deceptive about offering some and then also pointing out that you do this work yourself and would be open to a larger role with them.
It’s likely to be more effective if you wait until you’ve talked with the interviewers and established your expertise and helpfulness. Toward the end of that conversation, you could say that you’d love to be more involved and that if they end up hiring for the area, you’d like to talk more about whether you might be a match for that.
Also, I don’t know how much information they’re looking for from you, but there’s a point where it really should be paid consulting and it’s okay for you to raise that ahead of time. (A 15-minute call that you’re doing as a favor or to build your reputation, probably not. But something more substantial, yes.)
Related:
how to turn a request for free help into paid consulting
4. Using vacation at a new job, when it doesn’t roll over
After close to a year of searching, I finally received an offer to start a new role. Yay! My start date will be early November. Normally I know it is best to wait a few months before taking vacation days, which I usually do. However, I will accrue about 1.5 days by the end of the year and PTO cannot be rolled over, so I will lose the time I have earned if I don’t take it. Do I just have to suck it up since I’m so new? Wait and see what the culture is like? Or does not letting employees roll over PTO at year end mean places are more flexible with time being used? I would only want to use a day around Christmas, not the full 12 hours or whatever it comes out to.
If it matters, I don’t plan on taking any more time until the end of February/early March and even then it would only be three or so days, not a full week.
It’s very normal to take off time around the holidays even when you’re new, and a single day is nothing at all. (In fact, it would probably be no big deal to take the additional half day, too.) The exception to this is if you’re in a heavily coverage-based job and your coworkers already have dibs on those days.
After you’ve been there at least a few weeks, ask your boss about it. I’d say it this way: “I normally wouldn’t take time off when I’m so new, but I know I’ll lose my days once the year ends so I was hoping to take off X in December.”
5. Can I ask for a higher salary after I named a lower one?
I was contacted via email by a recruiter about a job that I think would be a great fit. The recruiter scheduled a time for a quick phone call to discuss the job. Unfortunately, she called right after I received a call to come pick up my sick kid from daycare. I was very distracted and ideally should have rescheduled. When she asked me my salary requirement, I told her an amount less than what I make currently. She then asked me to complete the job application online later, where I was also asked to provide a salary range. Silly of me I know, but I also put down that same number because I already told her the same thing.
I did the second interview where I was told the salary range and the top of the range is $60,000 more than I provided. Can I go back to renegotiate or am I stuck with the amount I provided? I don’t want it to seem like I only want more money now that I know their range.
You can still negotiate — now that you have learned more about the responsibilities of the job, you are envisioning $X instead of $Y. You don’t need to bring it up again yourself, but if salary comes up again or if it gets to the point of them making you an offer, that’s how you can frame it — “Having learned more about the responsibilities of the role, I was hoping for $X.” (And the fact that they shared their range with you, knowing it was higher than what you’d named earlier, is a good sign.)
Also! What happened that made you name a number less than you’re currently earning? That makes me wonder if you hadn’t been thinking about salary at all up until that point, maybe because you were thinking it wouldn’t come up that early, and so you were caught off-guard when the recruiter raised it. Use this experience to vow that whenever you’re job-searching, you’ll think about salary very early on so that you’re not caught off-guard if it comes up earlier than you’re expecting!
Related:
how to find out what salary you should be making
The post I can’t shake my crush on a former coworker, using vacation time at a new job, and more appeared first on Ask a Manager.
https://www.askamanager.org/2025/11/i-cant-shake-my-crush-on-a-former-coworker-using-vacation-time-at-a-new-job-and-more.html
https://www.askamanager.org/?p=34106