When Should I Have The DTR Talk?

“Define the Relationship” is a tough chat.

If there’s anything I’ve learned in my life, it’s that I’m full of shit when it comes to sticking to my intentions.

Only two weeks ago, I wrote about how I’m regaining power in my situationship with Jeremy. Meh. I have no power. Zero.

I’ve left too many comments about his “harem of women” that I’m not sure is a joke or a reality. Three in the past twenty-four hours. Each time, he laughed or glossed over it. Does he think that I’m joking because it’s so obviously untrue? Or is he brushing it off because it’s the truth?

All I have is a vague sense of Jeremy’s non-kid time. Our weekends without our children are on opposite schedules and I’m not switching mine (he’s not able to switch his) unless I know for sure that we’re exclusive. I pry for information about his weekends while balancing the act of not seeming too curious about who he is with and what he’s doing.

Is “drinking with a buddy” code for “drinking with a female that I’m fucking but we’re friendly so that counts as buddy”? Is he not responding for 12 hours because he’s busy with friends or his kids’ sports or is he spending the day with another woman? I overanalyze everything.

I cling to little bits of hope. Jeremy takes every moment we have an overlap of free time to see me. The last time he came to my place, he spent an hour doing home repairs while I insisted that he didn’t have to bother with any of it.

Today he joked that I sneak into his house in the middle of the night because he finds my dark, long hair everywhere (his kids are blond). If there were multiple women, he wouldn’t ask that question…right? Still, I make a harem wisecrack because maybe the other woman isn’t brunette. Dammit.

It’ll be a week before I can see him again because I’m doing a local getaway with some friends (a final “hurrah” for a friend dying of cancer). I tell him that my friend Ellie is flying in for this. She and I are going out drinking just the two of us this weekend. I slide in a comment about dressing slutty to go out, waiting for a reaction.

Jeremy suggests a beachfront restaurant to take her to. When I tell him later that it closes at 9 pm on Saturdays, he tells me “that’s not true, I went in at 7:30 pm and stayed until 10:30 pm”.

Really, Jeremy? You went to a romantic-looking rooftop patio and stayed for a few hours? My stomach is in knots. I use the opportunity to pry under the guise of restaurant operating hours.

“How long ago though?” I ask. He replies, “Two months ago? But I asked when I rolled in and they said they’ll stay open if there are lots of people.”

Two months. Nice catch. His approximation is kosher, whether real or not.

Am I being ridiculous? Yes, yes I am. It’s just shy of two months from our first date (but we chatted for two weeks leading up to it since he was on a fishing trip). I need to chill the fuck out.

I planned to have the dreaded Define the Relationship (DTR) chat when I got back from my mini girls’ trip. The basis would be planning weekends and how I’d casually say, “well, when you decide we’re done with harems and rosters, let me know and I’ll ask Joseph to switch custody weekends with me”. I’m making sure to include rosters so he doesn’t think he’s the only one with options.

Now I’m rethinking this plan. It’s still so early. I flipped when guys wanted this chat even at six months. But this is different. Jeremy and I click perfectly. I genuinely want to see him as much as I can. I hate leaving him. I never dread my time with him (which is a whole other issue; why was I dating guys that I dreaded seeing?). I let him sleep at my house, which is unheard of.

I research the best strategies and timelines for DTR. The consensus is anywhere between one to three months. The more difficult part is how to ask without scaring the other person away.

This is like a feral cat. If I come on too strong, it’ll scare him away. But I need to know how much time he needs. Do you need five months, bro? Okay, I can work with that because at least I know.

These are the best openers for DTR that don’t come across like you’re asking them to marry you:

“I love spending time with you…”

“I feel lucky we’ve gotten to know each other…”

“Spending time with you makes me feel…”

“I really like what we have going on here…”

“Just checking in on expectations…” (Yeah, no planet where I’m going to say this one.)

“I have so much fun with you…”

For me, I think options 1 and 3 work best. I want to switch weekends with Joseph but it’s a non-starter; I’m not overhauling the schedule for someone who isn’t exclusive with me.

On the flip side, what if switching weekends gives us more time together and we get even more time together? I don’t want to set a bad precedent, but I also want to give this relationship a chance to flourish without the constraints of only meeting on weeknights.

I’m in a foreign land. I feel like a teenager with constant butterflies and limerence. When people ask about him, my only reply is “he’s so pretttyyyyy I just want to eat his face, oh my gawdddd he’s so amaaaaazing”.

Yeah, I’m a lyrical mastermind when describing someone I like.

There is a part of me that’s scared. I went on so many dates to finally meet someone who had everything I wanted. Jeremy is a great dad. He has a good job and doesn’t drive a piece of shit, filthy vehicle. He has a fantastic career. He’s good in bed and I find him beyond sexy. He makes me laugh. Like genuinely, hysterically laughing with tears down my face. He rolls with the punches, is chill, and enjoys self-deprecating humor.

This fear makes me doubt myself. With the others, I knew I was whatever unicorn they wanted: loved sex, looks good in a tight dress, isn’t looking for a sugar daddy, and can hold a somewhat intelligent conversation. They were lucky to have me because I brought more to the table than they did.

Jeremy is different. Never has he made me feel inferior (if anything, he compliments me about things that no one else has) but my insecurities have me wondering if I’m at least unicorn-adjacent in his eyes.

Here’s what I know so far: he finds me attractive. He likes sex with me. He likes my abs. He spends time with me when our schedules permit. He makes efforts to help me around my house. He tells me I’m intelligent. He tells me I’m funny, especially in my writing (meaning my texts).

The butterflies are morphing into knot territory. Butterflies are good. Knots are awful. I need to reel this in before the knots take over and my anxiety destroys my body.