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Hello Captain Awkward,

Last month my husband and I (she/her) separated; it was my choice and I stayed in the home while he moved out. We were in couple’s therapy for several years leading up to the split and for the last part of the relationship we were living as roommates. For almost the last year, we were on opposite work schedules, so I only saw him 1-2x/week. I have no regrets about ending things and zero interest in getting back together. My ex and I are treating each other as kindly as possible during this transition and there has been no animosity/hostility. All my family and friends say I have been adjusting surprisingly well, but for me the relationship died a long time ago. I have discussed this with my individual therapist (“should I be more upset?!”) but she thinks I am taking good care of myself and I should not be anxious about something that I do not feel.

All this to say that I feel ready to start casually dating again. I have a great job, amazing friends, multiple hobbies/interests, practice self-care, and want to make the most of this summer. I am not looking for a boyfriend or anything monogamous; just looking to meet some interesting people, eat some tasty food, and start having sex again (it’s been months). I signed up for a dating app and started messaging guys which has been fun.

However, I am starting to have some anxiety about telling these men about my separation status as I fear they are going to judge me for jumping into the dating game so soon. I have not put anything on my profile about being separated. Part of me thinks that no one is going to swipe right when they see this, due to the stigma and because I am only 29 years old (“so young, so much baggage!”) Am I deluding myself? Should I be putting this on my profile and being transparent from the start?

I guess I hope once people meet me in person (and see that I am not someone who consistently whines about their ex/failed past relationship) they will not think it is a big deal. My plan was to tell people on the first or second date before too much emotional investment is made. I know I could easily hook up with guys who would not care, however I am not interested in having one-off sex with random dude-bros who only list their height in their profile.

If I should put separated on my profile, any recommendations for wording (besides “Separated BUT WELL ADJUSTED” haha)? The advice from my friends is split and the internet is no help. A lot of online advice says people should not start dating until after the divorce is finalized, but where I live you cannot file until you have been separated for a whole year, which is way too long!

Thanks,

Ready-To-Get-On-With-My-Life

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Dear Captain Awkward,

I’ve recently been making an effort to meet new people via online dating, and it’s been pretty great so far – I’ve met a few cool, interesting people who I enjoy hanging out and exploring potential romantic stuff with. Most of them have super interesting lives and a lot of cool stories to tell, which I like listening to. The problem is, they never ask me about myself and it’s starting to bother me!

I was raised to believe that it’s polite to demonstrate an interest in the person you’re talking to, and that asking them questions about themselves and their opinions is a good way to make someone feel at ease when you’ve just met. Plus, when I like someone, I usually WANT to know all about them and to collect as much info about this cool stranger as possible. The combination of the above means that on first dates I tend to spend a lot of time asking my date about the interests they listed on their profile, what they think about X global event, what they like to do in the city, etc., but I’ve started to notice that the effort is rarely (and sometimes never) reciprocated. This includes people who messaged me first and asked me out, so I know they’re interested in me romantically. I date people of all genders, so I know it’s not just an entitled dude thing (although the dudes are worse).

I’ve tried leaving pauses after a topic of conversation wraps up, for them to ask me something about myself (doesn’t work, they usually start telling a story about themselves or drag out the previous topic a little longer), and occasionally I’ll answer the question I just asked them uninvited (e.g. Me: “So where are your favourite places to hang out in the city?” Date: “Oh, I like X Y Z” Me: “Cool, I’ve been planning to check out Z sometime! Personally I like F and G”), but it makes me feel selfish to do this too often when they’re not showing more than a polite interest. I’m pretty sure it’s not shyness that’s stopping them from asking me about myself, because there are plenty of questions I ask them that they could easily ask back onto me (this is another thing that I was taught it’s polite to do when possible, but I accept that mileage may vary on things like this).

Plenty of these dates lead to a second or third date, and the trend of me feeling like I’m interviewing them continues even when we get to know each other better (or at least, I know THEM). Am I just dating assholes, or is there some script or social convention that I’m missing out on here? I’m not looking for a date to talk AT or for our dates to turn into back-and-forth quizzing sessions, but it’s starting to make me feel uninteresting and unappreciated!

Yours,

The Date Interviewer

Dear Dating Interviewer:

Hello, you are me from three years ago. Open to dating. Interested in meeting lots of people. Able to carry on a conversation with most anyone and put them somewhat at ease. Meeting a lot of basically okay people with whom I could pass a pleasant hour, but few kindred spirits. Meeting a lot of expectant looks across cafe tables. Feeling sometimes like I was putting on a show.

You could try keeping quiet for a bit and seeing if the other person jumps in, but honestly I think you should keep doing what you’re doing, but use it more as a screening process. If you get through Date 2, and the other person hasn’t asked you a single question despite you giving them many openings to do so, you know that they are not for you and there should be no Date 3 (unless they make all the effort to make one happen and make some kind of massive conversational rally). You can also say, explicitly, “I’d love to hang out again next week, why don’t you choose the place” if you’ve been taking more of the lead in planning stuff. The person will either rise to the occasion or not.

And when you run across someone who takes as much of an interest in you as you do in them, where it feels like a conversation rather than an interview, where things flow and it doesn’t feel like you are doing the work of keeping a conversation going, you’ll know you’ve clicked with someone. This is less about finding people who are interested in you (a lot of them are, and a lot of them will be) and more an exercise in finding out who passionately interests you.

Keep doing what you’re doing. Take breaks when it gets to be too much. Among the moths drawn to your flame, you’ll find someone who burns as bright as you.

<3,

Captain Awkward