When I first started OLD, I didn’t know exactly how to date with intention. But being on these platforms for six months, I’ve learned a lot about myself, what I don’t want and want, and online dating as a whole. I was wondering what are questions you ask when you date with intention? I don’t want to be overbearing with my questions but also want to make sure we’re on the same page about things we’re looking for. For me, I have a set of dealbreakers I screen for before we meet up. Very basic stuff (i.e. no smoking/drugs/etc.) and I own a dog and that they’re okay with that. My friends who don’t use OLD think I’m too serious and should just go have fun. I’ve been on these apps for awhile now, I’d like more productive dates and really would like to meet someone who I can share a future with (while having fun!) I also mentioned in previous posts, I think I have a pretty good profile now that reflects who I am. It shows the basic traits I want in a partner, my simple pleasures, my interests, I own a dog, and some of my core values.

I’m curious to hear what sort of questions everyone asks and how they go about deciding if the match is what they want. I’m looking for a life partner, someone who will be a good parent to my kids and share the same core values as me. The key thing for me is being family oriented, the other traits I’d like is caring, patient, down to earth… but primarily family oriented. Everything else, I can play it by the ear.

Thanks so much!

24 comments

  2. I think if you’re communicating all of this in your profile you’re off to a very good start.

    I’m guessing from your post that Hinge is the app you’re using. I’d make sure the guys I was looking for had Life Partner or LTR as their relationship goals. Anyone who says they’re “open to short” I’d move on from.

    The most important thing is that you’re clearly putting thought into this. I think a lot of people are like your friends with the “just go have fun,” and while having fun is necessary when you’re trying to date with intention, it’s not sufficient.

  3. I try to avoid the Q&A format and see if we can just enjoy each other’s company first. If we do, there will be plenty of time for questions.

    If you can’t vibe together first, who cares if they like your dog or not? Ya know?

  5. I think you’re doing just fine given your description. I do believe some people have 1000 must haves and are impossible to date because 900 of those needs are actually wants. I think some people throw themselves out there and pretend they can get along with anyone and end up divorced after years about arguing whether or not to have kids.

    Understanding yourself is key to any partnership and an asset in dating as it lets you focus on what you need and let go of what you don’t need.

    My current girlfriend loves wearing a robe around her house. Do I like robes? Nope. Does she ask me to wear one? Not really. Is this a big deal? Not even close. I’m amazed how many people would turn such a small thing into a larger issue by playing armchair psychologist about how robes relates to ambition or some other terribly loose connection.

    My only advice is try to find things to relate early on and remember their trying too. When you’re lucky you find someone who fills your needs, seeks to fill your wants, and you can reciprocate.

  6. If you get more than 1 match a week…. Banter for 1 session, then ask the big questions.

  7. >My friends who don’t use OLD think I’m too serious and should just go have fun.

    I’m not a picky girl but there are some basics they have to meet for me to have fun. Like how am I supposed to have fun with someone who smokes?

  8. I’m in the same boat as you. My friends have also told me to have fun with it, but “going with the flow” has usually met ignoring my own needs and allowing the guy to set the tone, which hasn’t worked out well.

    Since a lot of what you’re looking for are core character traits that are revealed over time, I’d recommend slowing down the pace of getting to know someone. You aren’t going to know someone’s true character after six dates, no matter how discerning you are. Communication is great but it can only take you so far.

  9. I think dating with intention means more like, if you recognise incompatibilities or dealbreakers early on, you would end it with that person and start pursuing other dates. When you’re just dating casually, you might not treat incompatibilities seriously since the goal is just to have fun, but with intention means to not let that glaze past you and instead being able to recognise and end it in a mature way.

  10. I usually leave questions for in person and never like to ask big stuff over messaging or video chat. I’ve had an awful video call once where they rapid fired questions at me like they had a script, but stuff too and by the end asked if I had any questions, I was gonna ask how many days off the job came with. Lol..so I tend to avoid that.

    The initial chit chat is just a vibe check and if we click I’ll suggest we meet. Sometimes the big questions for me are listed on their profile (desire for kids, ltr life partner etc) if not I’ll just ask in person, but only after spending some time feeling out the in person chemistry because there’s no sense in asking if it’s stale.

    I’ll ask things like “so why dating now or what brings you on [insert app]””where do you see yourself in 5 years?” “What’s your weekends like?” “What kind of hobbies activities you do for fun” something along those lines. I want to make sure our lifestyles align. Ive had times where I ask the why and where questions and the person freezes up and basically gets all quiet and awkward and avoids it or doesn’t want to talk about it, in which case that’s information for me.

  11. I usually leave questions for in person and never like to ask big stuff over messaging or video chat. I’ve had an awful video call once where they rapid fired questions at me like they had a script, but stuff too and by the end asked if I had any questions, I was gonna ask how many days off the job came with. Lol..so I tend to avoid that.

    The initial chit chat is just a vibe check and if we click I’ll suggest we meet. Sometimes the big questions for me are listed on their profile (desire for kids, ltr life partner etc) if not I’ll just ask in person, but only after spending some time feeling out the in person chemistry because there’s no sense in asking if it’s stale.

    I’ll ask things like “so why dating now or what brings you on [insert app]””where do you see yourself in 5 years?” “What’s your weekends like?” “What kind of hobbies activities you do for fun” something along those lines. I want to make sure our lifestyles align. Ive had times where I ask the why and where questions and the person freezes up and basically gets all quiet and awkward and avoids it or doesn’t want to talk about it, in which case that’s information for me.

  14. I definitely try to ask compatibility questions before we meet. Gives us both knowledge to build on.

  15. “dating for fun” is a big part of why everything is so fucked right now. Don’t let your friends tell you otherwise.

  16. I do think that OLD boils people down to a set of attributes almost like a video game character. Call me old fashioned but dating doesn’t need to be a science or some statistical analysis, standards and some non negotiable items are fine but humans are complex and nobody will fit someone’s exact mold of a perfect partner, and if they do they are likely suppressing some traits to appear perfect out of fear of their partner swiping onto the next one just because they like Pepsi instead of coke (seriously though who likes Pepsi)

  17. I’d say i date with intention, but i don’t really look to closely for long term things right away. I’d rather spend time to see if we fit well and get along first, and then after a little time decide if they are worth sacrificing things for. The more i am into them the more things i am usually willing to be okay with.

    How you evaluate partners should really only make sense to you, but it should be something to have an idea on. As long as your realistic about what you are looking for, there isn’t really a wrong approach.

  18. I have a very short list of questions that I ask on a regular basis. The rest comes with conversation and their actions.

    Have you been tested since your last sexual interaction? Is there anything that I need to know? It is surprising how quickly the conversations are steered towards sex by the woman. When they do steer it there then this question cones out. 90% of the women quickly disclose they are into some form of hookup culture and don’t get tested between partners. Needless to say I am not interested in someone who doesn’t take care of the basics like good sexual health.

    Do you want to meet up for a coffee and maybe a walk after? Quickly filters out women looking for free entertainment/food as the coffee date is to cheap for them. Eliminates women looking for casual online fun/validation. Coffee dates provide a substantial amount of information on a potential partner and gives a good indication of how serious a person is about their relationship intentions. I ask women this very early on usually by the second day of chatting or if chatting has taken up roughly 30 minutes of my time. I know its fast but once again the women looking for a actual healthy situation/relationship respond positively.

    I also tend to limit compliments to bare minimum until I meet the lady and I try really hard to keep the conversations PG. I got tired of the instagram offers, unsolicited pictures, sex chats, and group sex offers. Not hating on the casual scene but I find bedroom fun to be far more enjoyable when the person knows how to build sexual tension… they’re far more likely to be actively engaged instead of just… laying around.

  19. Guys perspective here and bare with me because I might rant a bit, but think of it like this;

    Before there was social media and dating apps existed, there was no such thing as dating with intention. You just went about your normal life and met people randomly through social circles or while you were out and about. If you happened to find someone you liked, you put time into getting to know them and maybe eventually found yourself in a relationship.

    For example my mom and dad have been married 35 years but randomly met at a club on army base. Realistically to this day, they are probably very incompatible and two completely different people yet somehow still managed to make it work and they’re happy. They didn’t write each other off immediately after 1 or 2 dates because of ‘red flags’.

    Don’t get me wrong, I do believe you should not lower your standards and to make it clear what you’re looking for, but I think the best way to date is to just meet people and go with the flow. Going into dates with ‘intention’ just subconsciously puts too much pressure on things even if that’s not your intent.

    Speaking as experience as someone who used to date with ‘intention’ but found to be forcing things when I know I shouldn’t have. I’m more laxed and things workout better when I don’t go into every date thinking “are they relationship material?”

  20. I’m very careful about the initial swipe as my problem has always been overlooking incompatibilities because I fall for someone who is great in some ways but not right for me. The apps help somewhat because I can occasionally get a lot of info before having direct interaction. As I am not able to enjoy multi dating, the process of meeting people without direction is too much time/work, so i do a very careful profile screen before swiping.

  21. I think having a brief but honest discussion about dealbreakers BEFORE a first date is key for me. I have a child and don’t want to have more (fine with me if the guy has kids) – these are my biggest dealbreakers and I need it to be very clear with the guy ahead of time.

  22. I take a pretty long time to get okay with an in-person date, and I prefer talking a fair amount before going out. Generally, my upcoming weekend is already booked with plans, and I only go on first dates over the weekend, so there’s some time to chat depending on when we match. Before I match, I’m generally looking for:

    Non-religious, mostly liberal/moderate, open to kids (flexible), drinks alcohol more than rarely, no heavy smoking or hard drugs, and monogamous (with an exception for bi women). I think that’s normally in a profile before matching.

    I feel like my needs are pretty easygoing, but I have some things I know are gonna mess up long-term relationships, so I ease in these questions into a conversation, not like a list:

    * Do you enjoy travel? Where and in what style? (I love to travel, but I’m not gonna be fun at an all-inclusive by the pool, or spending the whole time exercising.)
    * What’s your relationship with food/cooking? (I know I’m a bad cook – and I don’t like cooking or being cooked for, I want to date someone who is open to going out for food, or eating separately.)
    * What’re your cleaning and living space expectations? (I keep a house that can be a little cluttered, but not dirty, and I can’t date someone who is going to get frustrated with an unmade bed, a little bit of dust, or wants to be very minimalist. I get cleaners to come in every 2-3 weeks to keep things clean.)
    * What’s your approach to friends of the opposite sex? (I have friends that are women. Some are very attractive. I’ve known them for a very long time, and I can’t date anyone who is insecure with that. I’m dating you because I firmly believe I like you way more as a dating partner than any of them. Also, I want my long term partner to be able to have male or female friends without any major jealousy concerns.)
    * From my initial outlook on someone’s profile, religion is worth asking about. I won’t dismiss anyone on religion if it’s just a guideline, but if I or my kids would have to be a part of it, I’m probably out.

    Once I’m past these core questions, I think I’m cool with seeing how we vibe.

  23. Can someone please tell me what OLD means? I keep seeing it and i have no idea what it means lol

  24. dating with intention is way too overblown.

    have boundaries. have dealbreakers.

    don’t project long-term futures with relative strangers.

    also make sure your dealbreakers are *actual* dealbreakers — like people saying lack of a degree is a dealbreaker on the same tier as doing blow.

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