How Much Do You Spend Preparing For a First Date?

As I me last mentioned earlier in the week, I partook in a fair amount of retail therapy last tumblr_lgc91a0AUD1qg4ejuo1_500week. I spend the majority of my days in sweats and sundresses, so I look for opportunities to dress up. One of those opportunities are first dates. I tend to go all out. Which leads me to my question for today:

How do you (men and women) dress for a first date?

I can remember showing up to a date last summer and the guy was wearing a t-shirt, jeans, and sneakers. I felt insulted. To me, first dates are all about making a good first impression, and his lack of concern for what he wore absolutely turned me off.

While I give no thought to looking like maybe I’m trying too hard, I absolutely consider what kind of impression a lack of effort would make.

My next question for the peanut gallery is: do you go shopping or get your hair/nails did specifically for a first date? If you were to give an estimate, how much would you say you spent preparing for a first date?

Below are two examples of what I’d wear on a first date. Too much or just right?




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27 Responses to “How Much Do You Spend Preparing For a First Date?”

  1. fuzzilla Says:

    **While I give no thought to looking like maybe I’m trying too hard, I absolutely consider what kind of impression a lack of effort would make.**

    I’m too poor to get hair/nails done just for a date. In general, I try to fall in the “cute but not trying too hard” zone – cute shirt and skirt, a little extra effort with hair and makeup. I suppose I expect the same “casual but nice/well groomed” vibe from a date.

    Current BF wore a nice suit and tie to our first date and it intimidated me a little. Another guy from the same OKCupid crop showed up in a dirty T-shirt (he was telling me about his small farm and I guessed he was working on it that day, but it’s not like farming precludes bathing and laundry).

    I suppose if you’re talking a first date with someone you’ve never met before, you can kind of let the choice of venue be your sartorial guide (wine bar or ball game or what have you).

    • fuzzilla Says:

      **the “cute but not trying too hard” zone**

      I guess it’s kind of a balance between wanting to make a good impression yet keeping expectations in check. Going full “A game” on a first date means I’ll be that much more disappointed if it doesn’t pan out. Women on this blog have ranted before about, “I mean, I got a whole new outfit and my hair/nails done for this..?” I can see where they’re coming from. But obviously, making little to no effort is kinda having a bad attitude and setting yourself up for failure.

  2. Sherry Says:

    It depends on the venue: for a coffee house meet & greet, I’ll typically wear a cute blouse and some form-fitting jeans. The men whom I meet at the coffee house are also dressed casually in jeans or khakis.

    For a first date at a restaurant or upscale bar, I’ll wear a dress. I also get a manicure and pedicure.

  3. Bonjour Says:

    I usually decide what to wear based on the venue. Check out the place where you’re going to meet. If it’s a restaurant, google it and see what it looks like. If it’s an upscale place, I would dress the part. If it’s casual where people wear jeans and t-shirts, I would wear jeans with a nice blouse or a cute t-shirt, or a cute simple dress and accessorize it a little bit just to look cute without overdoing. Hair and nails should be done, and keep your makeup to a minimum. Most guys hate it when we wear lots of make up.

    Good luck!!!

    • Isambard Says:

      Saying “Most guys hate it when we wear lots of make up.” seems a little over generalized.

      I might go as far as to say that a complaint about your make up is a huge red flag. If guys didn’t like make up the whole advertising industry would look very different. Seems like control game playing to me.

  4. Nicki Says:

    I haven’t been on a first date in a minute and I’m pretty horrible at dating, but…

    Clothing: So I always base what I’m wearing off the venue. At a minimum in the summer I’d wear a little sundress and in the winter a cute sweater and jeans/pants combo with heels. Always heels. But I’m height impaired. That’s at a minimum. Now if we were going somewhere nicer then I would totally rock either of the dresses you posted above. I’ve just never lived somewhere like NYC so I think dating may be a little different. I think based on the dating that I have done in NY (don’t even ask!) those dresses are perfect!

    Hair/nails: I’m an every-two-week gel mani kind of girl anyway. So my nails are never naked and are always in good shape. Now if a first date fell on the tail end of a mani then I might move it up a day or two depending on the condition of my nails and the guy. My hair is pretty easy… Wash, dry, flat iron. I’ve never gone to get a blow out unless it was on the tail end of a haircut but my hair always looks nice (or so I am told).

    Makeup: Totally depends on what we’re doing and the time of day. My night time makeup will (obviously) be much more bold than my day time makeup.

  5. The Original D Says:

    Both those outfits would be great for a dinner date or drinks at an upscale place. A bit much if you’re meeting for coffee.

    • The Original D Says:

      I should add that I live in a super casual place where people do a lot of hiking, cycling, rock climbing etc, so both sexes tend to dress down.

  6. mxf Says:

    My favourite first date options are weeknights, ideally midweek, at a bar or pub. As such, I go straight from work and wear what I wore to the office that day. I generally go with a form-fitting dress and flats or jeans with high-heeled boots, depending on the vibe of the bar and what I feel like wearing that day. Either way, something that gives a an-easy-to-decode view of my figure up front. That way, you either like it you don’t off the top.

    Hair clean, blow dried nicely and worn loose, my favourite eye makeup or lip colour, nails short and neat but rarely painted, or if they are it’s a coincidence. Basically, I want to look like an appealing version of my day-to-day self, not the going-to-a-wedding version of myself. And I feel like men are likelier to form an overall impression (smells nice, smiles a lot, decent butt) than focus on individual details (didn’t get her nails done, hair wasn’t salon-sleek, etc).

    I expect the same general effort from a guy, but honestly, I’ve never sat down across from someone and hated what he was wearing. A lot of guys look good in a t-shirt and jeans.

  7. BTownGirl Says:

    I give those two dresses a just right! :) I’m the type who can’t NOT buy cocktail dresses (and if there’s a sale…please.), so I generally have something on deck. For super-formal stuff, I’ll usually buy something new, because sequins are good for the soul. As for nails, yup!, and for hair, my bestie is a stylist, so if she’s around, she’ll give me a blowout because I’m categorically incapable of competently doing my own hair. In the winter, there’s usually spray tans too. I guess it can get pricey, but I’m doing the same regular maintenance even if I’m not going on a date.

  8. Lisa Says:

    I never went shopping for first dates, nor did I get my hair or nails done specifically for the date. I keep up w/ regular nail and hair services so they always look fine, and I have plenty of clothes. I’m a single mom so I never had the luxury of time to just pop in for an impromptu service. But moreover, that was never my style. I don’t believe in going out of my way to impress anyone like that, especially not someone I’ve never met or barely know. That’s just trying too hard IMO.

    I might have worn the dresses pictured above on a first date IF our plans called for that. But most of my first dates were not fancy and did not call for that. Just a quick “meet and greet.” And I preferred it that way.

    I would def wear the dresses pictured above, tho, for dressier dates, after we had gotten beyond the first date.

    I’ve gone out on first dates in everything from 100 degree weather to the middle of a blizzard so my outfits have run the gamut. Basically just what I’d wear to meet up w/ gfs on a Saturday for dinner or a movie or drinks or coffee or shopping or whatever. No strategy behind it. Just look nice and go in w/ an open mind, expecting to have a fun time.

  9. NewEnglandMan Says:

    As a guy, I wear jeans or khakis with nice shoes and a button-down shirt on a first date.

    In terms of what a first date is wearing, my main concern is that it’s form fitting. And preferably form fitting pants. No butt-hiding long shirts, sweaters, etc. I want to know what her shape is. Even skirts like the ones pictured above, are going to hide a bit of form. With skirts or dresses, I can’t exactly tell how long her legs are or what size. These are things I don’t want to still be guessing at after a first date.

    The most important things to me on a first date:

    Her personality
    Her face and physique

    Getting hair and nails done for a first date are going to be lost on a guy like me. As long as my date is clean and well-groomed, I couldn’t care less about things like nails, make up, or jewelry. Maybe there are guys who do care about those things, but I think they would tend to be attracted to different types of women than I would be, anyway.

  10. Kyra Says:

    For me it really depends on the venue. If I’m meeting someone for the first time offline, we’ll lilkely be going for coffee or something lowkey, so I’ll wear nice jeans, a cute top, and heels. Depending on how I’m doing my hair it can take me anywhere from an hour to three to get ready.

    Now if it’s an evening date with someone I’ve already met, I’ll go all out and do a home spa day, hour long shower, do my nails, perfect hair and make-up, fix my eyebrows and wear a dress and jewellery and nice lingerie. Generally my dresses are wrap dresses that slim me down and give me that little boost of sex appeal.

    I love getting ready for a date, it puts me in this great mood, and makes me feel really confident.

  11. D. Says:

    I don’t think the question of pre-date cost factors in the same way for guys. Guys aren’t typically getting a haircut for a date. They might get one before a date, but they were probably going to get one in a few days anyway, if that’s the case. Likewise, they’ll wear clothes, but they aren’t really going out and buying clothes specifically for a given date, or necessarily for dating in general.

    I suspect that most men are more likely to spend money on the date itself than in preparation for it specifically. As an example, the woman above who mentioned going out with a guy who showed up in a suit…he didn’t buy the suit for the date. He had it already and would wear it again some other time.

  12. Noah Says:

    Speaking from the male perspective, we really appreciate it when women make an effort. And I would give an enthusiastic “thumbs up” for either dress in the pictures. As another poster commented, context matters – so if our first date is something casual like a coffee house, then perhaps these outfits might be a bit over the top.

    That said, whether or not it is a coffee shop or a night at the opera, I do my best to be clean, well groomed, and fashionably appropriate for where we are going. I have noticed since I am over the age of 40 that younger guys are not as fastidious as I am, and perhaps that’s partially a function of fashion or maybe it’s a generational thing.

    I will also admit to being much more likely to after some unsatisfying experiences being more likely to keep the first date or two casual and low key before committing to inviting someone out to a more expensive fancy event such as going out to dinner or going to a show.

    As with many things in life, it depends on the situation and everyone’s experience will likely be different.

  13. Lucy Says:

    I always try to make an effort. I don’t know if I would dress to the nines, but I always put on a nice dress (preferably red) and do all my make-up and nails. I think it’s showing consideration to the other person that they are worth your effort whether it goes any further or not.

    I once went on a date with an okcupid guy and I think he was too busy to put effort in, like he was fitting it into his busy schedule. He looked a little frazzled and scruffy and his hair wasn’t combed. It was a weird date because he made zero effort. I had to lead conversation, suggest the next place to go etc. No planning whatsoever and he was the one who invited me out. Perhaps it was just a practice date for him to put himself out there. But I was a bit mean afterwards because I blocked him when he messaged to say “That was fun. If you ever want to hang out again, let me know”.

    So yes, making an effort to look good makes a good overall impression (like it does in a job interview). I love your dresses, Moxie. They are really classy – not too much at all. Plus they look good for both day and evening.

  14. Jake Says:

    Well, if you wear a suit and tie on a date make sure to undo the tie. Otherwise, you will look stuffy.

    Also, not a good idea to not recognize the effort a woman puts in to make a good appearance. A lot of women will have their hair and nails done for a date. If she does this, contrary to what New England man says, you should be impressed and tell her she looks great or something like that. I mean, she could have just shown up wearing shorts, no makeup or after hitting the gym. Those girls I uniformaly rejected after the first date.

    • RC Says:

      Say Angelina Jolie (insert your favorite celebrity) look-alike showed up to an afternoon date with you in gym clothes…and you clicked… I would bet you won’t hold the grudge ;-)

      I think that if we like the person we will forgive first day appearance. If we don’t immediately like them then priming is important.

      My personal preference look-wise was clean and looks fairly similar to his pictures – the rest was personality, conversation, laughs and chemistry…

      And finally – what one person considers hot another might think of as meh…
      My first OKC date with my now husband was in the summer. I was in shape and wore bakcless summer dress I loved – I thought I looked great! Later, I found out he thought I was wearing a mu-mu… But we clicked.

      • Jake Says:

        I don’t see myself going out with Angelina,so not relevant. I too, went out with a woman who wore an off the shoulder and free flowing dress. I thought it was a mu mu, too. Her apparel did not improve much over the course of our dating. Also, what she wore was always either black and white or a combination. Compare that with the woman I am saying now. She dresses chic and sophisticated. I like that and it means she will fit in at business rated functions.

  15. bbdawg Says:

    Always a dress and some kind of heel but making sure I am not “trying hard”… I love make-up and spend time on my hair so that tends to get most of the attention. I tend to actually NOT care too much about first dates, just as a way to not get expectations too high initially, so shopping is not a priority. Come to think of it I might actually have a couple of “first date dresses” which I tend to stick to on all first dates.

  16. Maria Says:

    I love to wear dresses! Really like the dresses on the pictures especially the black dress. I usually like to wear something elegant on a first date similar to the dresses you posted.

    I once went on a first date on Saturday at 1pm after my dance class, so had trainers and a casual dress on, just didn’t want to carry anything extra with me. Then it started raining, we did a lot of walking around that day, so my hair went mad, makeup ran. Next date we went to play badmington, so I had trainers on again lol. I started wondering when will I get the chance to look more elegant?

    But the dates were so much fun! And we ended up going out for 6 month. I don’t think it matters that much whether you are dressed upscale or a bit too casual on a first date but you definitely must wear something that makes you feel good.

  17. Maria Says:

    I have a first date dress too! :) I remember thinking oh it’s great going on first dates I can wear the same dress on different nights out and not worry about it. Maybe best not to go to the same bar though lol

    I like to stick to the rule on the first date that it’s either legs or cleavage but not both. And it’s just a little bit of cleavage, they will be staring down your top for sure, but no need for a full view just yet ;P

  18. coffeestop Says:

    It depends, I am meeing somebody for a first date at a local art gallery next week that has some nice gardens and walking paths outside. I think I will wear a casual skirt a cute top and ballet flats in case we explore outside. I will wear earrings but not go nutty on the jewelry. When we met I was wearing a similar outfit so it will seem appropriate I guess. I am not sure how much men notice this stuff. If it was dinner/theatre type stuff a nice dress, heels, get the nails done. I have a girlfriend date with a friend tommorow for the theatre and she is stylish so I will have to look decent next to her. I am pretty middle of the road fashion wise.

  19. Camie Says:

    I always like to make the best impression I can and I tend to wear one that shows my legs. I take the place where we’re meeting into consideration but I’ve never been a casual person and feel comfortable even when I’m the only one in a dress.

  20. PGH_Gal Says:

    I think there is an age factor and a location factor to consider. I have lived in a variety of cities and NYC or DC is definitely a dressier kind of crowd. I now live in Pittsburgh and, well, let’s just say that I’ve met a guy for a first date who was wearing cargo shorts, black socks pulled up to mid calf and a Tommy Hilfiger polo shirt circa 1996 (I actually remember a friend had this shirt in high school). Now based on age alone (he was 36) I found this unacceptable and was immediately turned off by him. I politely had a drink and then called it a night.

    However a “well dressed” date here, in my age range (I date late 20s – mid 30s) would be wearing a button down and a pair of nice jeans with cool shoes. I do my own nails and I’m pretty meticulous in that department on a daily basis, so I’d just do a double check for the date night. I don’t go shopping for a first date, but I’m definitely one to wear a dress and heels or wedges. I just like the way I look and feel in a dress, so that’s the direction I’ll always go in.

  21. maria Says:

    I have been on so many first dates, i stopped doing anything special like mani pedi or shop for them. i save that stuff for later dates.

    i make sure i am showered, hair is nice and not in a messy pony tail, i wear plenty of make up for sure and something neat and nice like a cute dress and nice (comfyish) shoes but nothing like the pictures you added. Mostly its because I feel really crappy if the guy shows up in sloppy casual clothes and I am dressed up. but it is also because i work in a pretty casual environment and almost all of my first dates have been after work on a weekday, not weekend type of things where i have time to get ready. I go straight from the office to the date. I get upset when the guys put zero effort–and most of them don’t and show up in ugly jeans and tshirts and ugly dirty dad sneakers when I made an effort. I don’t expect suit and tie, or anything like that. even a nice pair of dark jeans and a button down shirt would suffice. I find that it shows little to no respect or care/interest in the date. the few guys i have hit it off with and ended up dating put a little effort into what they wore–button down shirts and decent pants and shoes etc. my current wore a button down shirt, slacks and a jacket to our date and it immediatley made me feel that he wanted to be there and that he wanted to make a good impression. that wins points with me.

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