Q:

Single lesbian here who is in desperate need of some dating advice. The backstory: I’ve been in relationships before, but they were usually the result of a setup/mutual friend/etc. None of those relationships lasted much longer than a year, my longest was probablyyyyy 16 months? I’m 34 and not freaking out about getting into a relationship quickly or anything but I just feel like I’m doing something WRONG on first dates or thinking about them wrong or otherwise failing at something that I feel like I used to have a better grasp on. I’ve been single for a year. I don’t need a partner right away, but I’d like for something to progress past a first date or even to just progress to a hookup. I’m lonely. And looking to date someone or multiple someones and have some fun.

The problem: I am no fun on dates. It’s like I freeze up and forget how to be a person. I’m a friendly, capable, smart person in all other parts of my life. I have friends. I know how to hang. But on a first date, I become the most boring, timid, and anxious version of myself. And I feel like it starts before the date even begins. I have SO MUCH PRE-DATE ANXIETY that I just let dominate my entire vibe leading up to and during the date. As a result, I have a trouble turning a first date into a second and also feel like I can FEEL my date getting turned off. Needless to say, the date rarely leads to a steamy moment or a second location. And that’s rarely because I’m the one to end the evening.

My usual methods (and meds!) for dealing with this kind of anxiety for some reason don’t work when it comes to dating. It’s like I build the whole thing up in my head, wanting so badly for the date to lead to something more or at least for someone to I don’t know what to come home with me that I then overthink the whole thing and decide no one would ever want to come home with me and then in turn……self fulfill that prophecy. I can’t seem to break this cycle. I don’t need you to fix me, but I would love like a few tips on how I can CALM DOWN before dates and not be so in my head (other than the obvious like meditation, journaling, etc). I need tools! I don’t want to fuck up more first dates!!!! This is not the reputation I want!!!!!!

A:

Well you have made my job harder by taking away my go-to piece of advice in pretty much all situations (journaling lol) but I shall TAKE A STAB HERE!

Pre-date anxiety is normal. Your anxiety management strategies not really working for this particular brand of anxiety is also normal. Dating is its whole own social experience, and while some people can approach it in a similar way to hanging out with friends or other forms of socializing, that doesn’t work for everyone. So I’m not going to tell you “just treat it like hanging out with a friend!” because I don’t think that’s what your anxious brain needs to hear. But I do think there are some tangible/practical/specific things you can do in order to take some of the pressure off of first dates.

My first suggestion would be to work on reframing your mentality about dates by detaching from predetermined outcomes. This is actually advice I give to people when it comes to creative rejections, too! For my writer friends who struggle with constant rejections, I tell them to treat the actual act of submitting the thing or applying to the thing as an accomplishment itself instead of only attaching value to the possible outcomes. I tell them to get themselves a little treat when they apply! And when they’re rejected! It’s small, but it provides a bit of dopamine in those moments and also helps them work on realizing that just the act of applying signals growth, determination, ambition, and momentum in their creative lives.

In a similar way, I think you need to (obviously) focus on the date itself rather than any potential outcomes you’re hoping for. Going on a date is fun, exciting, and also requires vulnerability and intention on your part! That’s an accomplishment in and of itself. Hey, I know plenty of people who struggle to even PLAN a first date, so you’re already one step ahead of that. If you’re getting overly worked up about the idea of a first date ending quickly/not leading to a second location/etc., I agree that this overthinking could be exactly the reason dates are indeed headed in that dead end direction. What if you set yourself up for success by making potential post-date plans with yourself or with a friend? Set an “after date” plan for if a date ends early where you go get your favorite post-dinner treat or meet up with a friend to hang out, debrief, and remind yourself you can indeed hang! (If you’re worried about basically keeping a friend “on call” for this sort of plan, I can assure you I definitely wouldn’t mind doing this if a friend asked! And I’d be happy for them if they had to cancel because the date ended up going longer!)

It’s possible that the thought of coming home alone (not sure of your living situation) after a date is holding you back before and during the date, because you’re scared of that feeling of loneliness and a comedown. Because that’s really what that can feel like! A crash out after a surge of tingly feelings from meeting a new person who you’re attracted to! So have a plan for yourself after the date, whether that looks like going out solo or with a friend or even just deciding on a movie you’ll watch and self-care treatment you’ll do at home to make that comedown feel a little less abrupt. Maybe with time, this type of routine will help you feel better after a date, no matter how it ends, which will in turn make you feel better before, too, because you’re not stressing yourself out about what it will feel like to come home alone.

Crowdsource your friend group for their favorite questions to ask on dates. Get dating advice from other people! Of course being yourself is important, but asking for advice and ideas won’t result in a performance; it’ll just give you some starting points for how to direct conversation and energy at the date when your brain is in an overwhelmed state. You don’t need to dazzle your date or charm them from the get go. Ease into it, follow their lead. They’re likely experiencing a bit of anxiety, too, a lot of people are on first dates! When in doubt, ask them about themself. That’s always a sexy move and a way to keep the conversation going.

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There is also nothing wrong with saying “first dates make me anxious.” That’s not a turnoff imo! Sometimes getting it out there takes away some of its weight. It also allows the other person to share if they’re feeling anxious, too.

Are there settings for dates that would make you feel more comfortable? Times of day? Like if you plan for a date right after work, does that almost give you less time to spiral? These are just hypotheticals; I don’t know the exact contours of your anxiety. But if there are logistical factors that would make the dates feel a bit less intimidating or overwhelming (quieter settings? LOUDER settings?), you can always pick locations, times, days, etc. based on that.

I’m not going to tell you to relax. That’s the worst thing to say to someone experiencing anxiety lol. Don’t beat yourself up over this normal and typically uncontrollable state that’s happening to you. That’ll only make it worse. Just try to not get attached to any particular outcomes of a first date. Give yourself something nice to do when a date ends. Talk to other people in your life about their own dating advice. You don’t have to feel like you’re alone in this.


You can chime in with your advice in the comments and submit your own questions any time.