Is it fruitless to pursue someone who has a boyfriend?


anonono-nonono asks:

Is it fruitless for me to pursue someone who has a boyfriend?


A month ago I started a new job, where I met a co-worker (let’s call her F) who fits my type in terms of both looks and hobbies. After making friendly chats with her for a week or so, I asked her out on a workday lunch together, which she accepted. It was at this point that this other co-worker (let’s call him G) mentions that F has a boyfriend. At the time I figured “hey, I didn’t hear that from F directly, so may as well test the waters”. The lunch went better than I thought it would, considering my level of conversation-making. I tried pitching a weekend date but got refused though. A few days later I asked her out for lunch again, but she said something along the lines of “let’s invite other people too” (a death sentence), and at said lunch F and G (who happens to be gay) started talking about their respective boyfriends. G later said it was unintentional, but the whole scene was clockwork, I tell you.

Now the question is, if I want to pursue her still, how should I approach the situation? I’m aware that I would be selling my soul to the devil by splitting up a 2-year (intel from G) relationship. I’m also aware that I shouldn’t put my eggs in one basket, as I’m considering this a side plan while preparing to meet other women.


Demetrius says:

Funny that the word used is “fruitless”. People tend to think of and use this word as an adjective (i.e. not producing the desired result), but I like to think of it more in a metaphorical sense. Your actions will always bear fruit. I think that pursuing someone, whether they are monogamously attached or not can always bear fruit, though that fruit might be bitter once you taste it.

Here’s a very abbreviated version of one of the times I pursued a woman who had a (supposedly monogamous and committed) boyfriend. We met, and I knew she had a boyfriend, but I pursued her anyway. We hooked up, she stayed with him for about a month or so while we were ”dating”, and eventually she ended things with him. We dated for a bit, then she left me unceremoniously, and I was ruined romantically for a while. Technically speaking, pursuing her bore fruit, but that fruit was bitter as fuck.

I think pursuing anyone (or anything for that matter) can bear fruit, but you have to ask yourself if you’ll want what you get. Sometimes you get exactly what you were looking for and realize you don’t like it, and sometimes you get a twisted version of what you wanted. I won’t make a moral argument against pursuing someone who is attached because telling people to do the right thing rarely works, so instead, I’ll just tell you why you shouldn’t pursue this woman, in this specific situation:

She’s not interested in you


Putting aside the morality of pursuing someone who appears to be in a committed, monogamous relationship, I don’t see how anything in the situation above even remotely sounds like a green light. You had a business lunch with a coworker and had a genial conversation. Congrats on that, building new work friendships can be tough, but uh, what else was there? Seriously, re-read the question if you like, and you tell me where a promising sign can be found because I am seeing exactly none. No mention of flirting whatsoever, and the one time when you actively tried to indicate romantic interest, it was firmly rebuffed. The next time you tried to get her alone, she realized what your intent was and asked to invite multiple people to act as a buffer between you. You even called it a death sentence BECAUSE YOU KNOW SHE ISN’T INTERESTED. Outside of her wearing a shirt that says “Bro, I do not want to date you, at all, in the slightest possible way” I can’t think of any other way she could be clearer that she has no interest in dating you.

Listen, I’ve flirted with, and had a dalliance or two with attached women and trust me, if there was interest there, you’d know. It’s not playing hard to get so much as it is very frankly rejecting you. If you’re wondering how to pursue her, don’t. Again, morality aside, you’re considering pursuing an attached coworker who has had opportunities to show romantic interest in you, and has chosen not to. You’re not selling your soul to the devil, you’re shitting where you eat. You’re not “putting your eggs in one basket” you’re trying to put your eggs in a basket and she keeps slapping them out of your hand. This is a terrible side plan while you prep to meet other women because:


Is not.

A woman.

You have a shot with.


Instead of focusing on someone who has never shown interest in you, maybe try to meet someone else. Preferably someone who is available to date you.

Good Luck Out There.

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