I just got out of a long-term relationship, and am ready to date (something I’ve never really done). Quite a few of my guy friends are now showing interest in me that is more than friendly. While I don’t want to be in another relationship anytime soon, I would like to see where things might go with one or two guys. Is it a bad idea to start seeing guy friends, especially if I don’t intend on making a commitment right now? Should I stick with strangers?
Dear Feelin’ Flirty,
I think the answer to this is a bit mixed from my end. I want to say maybe you should do this, but I also want to tell you to never, ever do this.
I will start by saying that there is no case, in the history of time and male-female relationships, where a friendship with benefits has ever been completely benign and innocent — where no one got hurt, jealous, confused, or heartbroken. There are, some cases where people eventually get over that hurt and confusion and move on to continue as friends – but the heartbreak and jealousy do still occur. It’s only the least needy and attached types among us that can achieve this balance, and still only after a bit of hurt and pain first.
I stress that this is something to know and be aware of so you don’t go blindly into something that could end up hurting not just you but someone you care about as well.
That being said, there are some situations in which I think you should do it:
1. If he’s more of an acquaintance than a good friend.
The damage caused from a ”with-benefits” friendship might not really matter to the future of your relationship if the friendship is relatively surface-level and not the lifelong type. Meaning: if you don’t care more about staying friends with him than you do about the possibility of getting down and dirty — then by all means, give it a whirl!
2. If the flirtation coming from your guy friend seems relaxed and confident.
What you really don’t want is a guy friend who has been secretly in love with you while you were in your relationship and is now looking to take things to the next emotional level — while you are really just looking to explore your options, flirt, and have fun with your newfound freedom. This is a disaster waiting to happen.
3. If the conversation is open.
Open communication — to a level where you can be extremely honest (and kind) with each other about your boundaries, expectations, and current desires for committed relationships — has got to be there. If you can’t talk honestly (that being the key word) about what you really want, it will NOT work. If one of you is fibbing, at any time, to spare the other’s feelings, you will undoubtedly end up hurting each other more in the long run. So make sure you can have a conversation about what it is you’re really doing. (Are you sleeping with other people? Are you exclusive when it comes to sex but have no responsibility to each other besides that? Etc, etc.)
4. If he is just so damn good looking that none of the above matters…
…then who cares?! Live out your fantasy, woman!
If you can check all of the boxes above (except maybe #4), you may be able to have a healthy, honest, and fun friendship with benefits. If you are feeling like you probably cannot do that, then stopping that friendship from quickly turning into a full-blown relationship will be tough. And I think, from the phrasing in your question, that’s probably something you don’t want right now.
I am wholeheartedly on board with dating as much as possible after a serious and long-term relationship. The women who seem the most lost on the journey to finding their true selves are the ones who consistently bounce from boyfriend to boyfriend and never take a pause to reflect on who THEY are when there is no one else standing next to them.
So, if you can make it work, go for it! But if you think that maybe there’s a chance this could go terribly wrong…trust your gut and stick to a strictly platonic co-existence.
You don’t want to end up singing this at the top of your lungs while crying on the side of the road in your car.
(Not that I have any idea what that’s like…just a completely random and totally not-related-to-me example.)
Friends don’t let friends date their friends (unless they can stay friends),