“I recently reconnected with my first girlfriend [27F] from 13 years ago. We dated on an off throughout high school and had a few “flings” while I was in college. Nothing really ever stuck but I’ve always had this lingering feeling that she was the love of my life. She would always come back into my life out of nowhere and we would reconnect for a while and then it would fade and we’d stop speaking for a while. Most of the time this happened was because I would get tired of her not wanting a relationship and I would move on. This last time, we hadn’t spoken for 5 or 6 years. I happened to reach out to her recently just to see how she was doing with no intentions other than that. She happily spoke to me for about two days and then became quiet again until the other day when she asked me to come spend the night with her. She’s been fairly talkative since then and seems to be happy to be speaking to me again. Given our history, I’m not really certain how to approach this but I don’t want to hurt her as I’m afraid that after every time this happened in the past I may have hurt her without realizing it.
I also met a girl [21F] recently as well. We’ve been spending a lot of time together and whenever I’m with her she makes me feel incredible. She’s very affectionate and loves to talk about everything going on in her life. However, when we’re not together, she doesn’t seem to be as interested in me as when we are. Very brief texts where it seems as if she doesn’t seem to care to be talking to me. We haven’t made any commitments toward each other yet as we are still getting to know each other and would like to spend several months trying to see if we are a good fit before moving forward due to both of us being in relationships with shitty people in the past whom if we had spent more time getting to know them we wouldn’t have ended up in those poor situations.
27F knows I have been seeing 21F, and 21F and I started spending time together AFTER I reached out to my ex, and it was a while before my ex reached out to me the other day. 21F and I are both aware of us not being exclusive at the moment yet we have been spending more time together than with anyone else as there has been more time that we have spent together than apart.
What I am asking here is advice on what to do in this situation. I don’t want to hurt either of them, but obviously that’s probably not possible at this point because I made the decision to go spend the night with my ex. Some people might consider this cheating but I am not in a relationship with either of them and I have specifically stated that they know of each other to hopefully deter those sort of comments. If there is any more information that anyone would need to help me here I will be glad to add I am just not sure what else I would need to say at the moment.”
TL;DR – I am currently “seeing” two people at the moment, they know about each other but not who the other person is, and I need advice on how to move forward considering both their feelings and my own.
In modern dating, the basic assumption is that you are non-exclusive with each other until you have the exclusivity talk. Exclusivity talk essentially goes hand-in-hand with the Define The Relationship (DTR) conversation where y’all flesh out what this relationship means to each of you. Until then, it is perfectly ethical to date more than one person at a time.
Let’s first talk about your connection with 21F.
With that being said, I can understand your fears of hurting either 21F or 27F. Considering that you are spending a lot of time around 21F and that 27F already knows about 21F, it might be time for 21F to know about 27F as well. It probably doesn’t need to be a full-on discussion, but your connection and history with 27F warrants at least some form of disclosure to clue 21F in on where your headspace is at. She can then continue to opt into investing her time and energy in this connection with you with informed consent for herself.
You also mentioned that you’d like to “spend several months trying to see if we are a good fit before moving forward.” That is a long time. I wonder how much of that perspective is informed by your current happenstance and also you fear of hurting 21F. You need to acknowledge that asking someone to invest several months of non-exclusive dating is a big ask, especially with the amount of time you and 21F appear to be spending with each other. At the very least, you need to communicate this expectation and timeline with her so that she is also in-the-know about what to expect from you in these coming months.
Now let’s talk about your connection with 27F.
There is a lot of history here between you two. But like I said earlier, you did the right thing by disclosing to 27F what she should be expecting from you with your budding connection to 21F. The best (and maybe the only) thing for you to do here is to continue to communicate and stay connected with 27F. There is a definitive push-and-pull game between you and 27F that really intrigues me. You appear to acknowledge her intentions but hesitate to verbalize them with her. Case in point, you mentioned that you’ve had problems with 27F in the past when she did not want to commit to a relationship before you moved on. Have you considered discussing how that on-and-off connection has pervaded throughout your thirteen year history together? And thirteen years is a long time.
Admittedly, it has been five to six years since you last reconnected. So things may be different. She probably was a completely different person when she was 21 or 22. You asked for advice on how to approach this situation, so I’ll give you some advice.
Set your foot down and establish some healthy boundaries with this person.
Healthy boundaries could look like determining for yourself what you are and are not willing to tolerate from your friends or potential partners. It could mean refusing to go over when she asks you to keep you company late at night. Mindfully assess how you feel about this, then intentionally approach your next steps with care and conviction. You’ve been on this ride for the past thirteen years. Ask her how this will be different this time around, and pay close attention to how things are actually different this time around.
You say you’re afraid of hurting her. Let me turn that around and ask you aren’t you afraid of her hurting you?
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