We’re talking to five online daters to get their views on a very important aspect of online dating: meeting someone (IN PERSON) for the first time. Check out part one of what they had to say about their best first dates, what to wear, and their biggest fears about meeting up with an online love interest – in the flesh!
What’s the best first date you’ve had with someone you met online?
I took someone to a day date at MoMa once. It was nice and I scored intelligence brownie points.
What’s your biggest fear when you go on a first date with someone you met online?
That you’ll meet somebody that looks/is nothing like advertised. It’s annoying because you spend so much time getting to know someone beforehand and given short time constraints in NYC that becomes annoying
What do you usually wear on a first date?
Depends on where we’re going, but most time I’ll wear all black.
Tell me about the weirdest or worst first date you’ve had with someone you met online.
So many… One time the guy was actually 30 years older than his picture, another time I got trapped in a 3 hour dinner with the the world’s most boring man? Prefer not to think of those 
In your experience, do the people you meet look like their profile pictures?
80% of the times they don’t. The degree of disparity varies though.
What’s the best first date you’ve had with someone you met online?
I’ve actually been on a lot of great first dates with people I met online. I love meeting people and unless there’s just nothing in common I usually try to have a good time whether or not I’m attracted to them.
The best one of all though, hmmm…. I was living in a guest house in Topanga, CA. We’d been talking online for a while – but he lived in another city. We finally arranged to meet – at my actual place. He showed up, we went down to my woodpile, and he split some and stacked it to replace the armload we each then carried up the hill. We built a fire, cooked dinner from my CSA box, listened to music, had sex – and he hasn’t left since.
What’s your biggest fear when you go on a first date with someone you met online?
That they will reject me because of the shape or size of my body.
What do you usually wear on a first date?
I work from home and don’t give a shit, and often go out in my pajamas, so I have pathetically few flattering outfits. I actually have a series of date outfits, specifically so it doesn’t look like I’m wearing the same thing every time, and I keep track of the sequence of them, lol. I usually wear leggings, a short skirt, and a V-neck long-sleeved shirt.
Tell me about the weirdest or worst first date you’ve had with someone you met online.
Mostly they’ve just been boring. I seem to be the kind of person that people trust, so a lot I’ll get told really strange deep secretive stuff on a first date. Recently a bisexual date told me that he went on a date with a man just to have sex, but then there was an additional man there when he got there that was older and a friend of his father’s – and that he went through with the sexual activity with both of them anyway out of some sort of weird obligation – and he didn’t feel good about himself for it. That’s definitely a weird thing to hear on a first date.
In your experience, do the people you meet look like their profile pictures?
Yes, mostly – there’s usually some resemblance. Except this one guy I went on a date with a few weeks ago looked all pudgy in his profile photos and was in ridiculously toned shape when I met him in person! He’d just not bothered to change the photos, which made him all the more hot to me because he wasn’t sorting for women who care deeply about how toned his body is, nor was he getting healthy and toned for the sake of the way it made him look, rather how it made him feel.
What’s the best first date you’ve had with someone you met online?
There’s been a couple that I’ve been on that I’d entered with zero expectations, and they turned out to be genuinely good times. They didn’t materialize into much, but it was fun getting to know and spending time with some new, interesting people.
What’s your biggest fear when you go on a first date with someone you met online?
That it will be incredibly awkward, they don’t look anything like their pictures, they’re serial killers. You know, the usual.
What do you usually wear on a first date?
Nothing too fancy. Jeans and a cute shirt. Maybe some boots.
Tell me about the weirdest or worst first date you’ve had with someone you met online…
I luckily haven’t had any horror stories. Maybe I’m due for one now? I had one date that there was just no chemistry there at all. I felt like I couldn’t get out of there fast enough. I basically chugged my beer looking to speed things up, but he really nursed that bad boy. I counted my lucky stars afterwards that we never exchanged phone numbers. We had only communicated via the dating sight, so there was no opportunity for any post-date uncomfortable texts.
In your experience, do the people you meet look like their profile pictures?
I think most of the guys in have met generally look like their pictures.
What’s the best first date you’ve had with someone you met online?
I went on a great first date over the summer with a girl that said she was down for anything as long as it was outside. We met at a coffee shop and bought drinks to take outside. We walked and talked for a few hours and wandered around until we found a street fair. A photographer took our picture and asked how long we were dating. We said several months and laughed about the lie. We grabbed dinner at a restaurant that played silent movies on a big projector outside. The rest of the night we spent bar hopping and eventually cabbed it home. We made out in the back seat and parted ways.
What’s your biggest fear when you go on a first date with someone you met online?
The thought of having nothing to talk about or dating someone whose easily offended sounds like a nightmare to me. The idea of the date being awkward and uncomfortable is enough to make me want to get the check quick and split.
What do you usually wear on a first date?
If you choose a laid back watering hole for a drink, you may just wear what you wore to work or plan to dress a little less casual by sporting a nice pair of slacks or shoes. If the date seems a bit more formal and you have dinner reservations, a sports coat partnered with a button down and clean jeans is a solid choice. Usually, you can’t go wrong with a clean button down, a pair of jeans and your favorite boots.
Tell me about the weirdest or worst first date you’ve had with someone you met online…
I once went on a date with a girl that had used photos of her roommate as her profile picture. When I arrived at the bar to meet her I was approached by a random girl I had never seen before who knew exactly who I was. I later revisited her profile and discovered that she was indeed featured in her profile photos – only in the background, out of focus and completely in shadow. Needless to say, it was a disappointing discovery and despite being catfished I had a decent time talking with her. This was however our first and last date.
In your experience, do the people you meet look like their profile pictures?
Other then the date mentioned above, the dates I’ve been on have always looked like the person represented on the profile. I will say that usually the person is never as good in person then their carefully selected photos that they think represent them. There is also a trend with some women to feature older photos that show them in a more flattering light. This usually comes down to images of themselves before a noticeable weight increase. Not always but sometimes.
What’s the best first date you’ve had with someone you met online?
Hmmm…well there are fun first dates and there are “best” first dates. I think the best dates are when you really feel like you clicked with someone by the end and you know you want to see them again. When that happens it doesn’t really matter what kind of date you went on. I think on my best date we just kind of bar hopped and then made out outside of the subway for a while.
What’s your biggest fear when you go on a first date with someone you met online?
That I will be bored. The worst is when you are on first date and two minutes in you realize that the other person can’t carry a conversation. I went on a first date last Sunday and here is how the beginning kind of went. Me: “So you grew up in Italy, what’s that like?” Her: “It’s fine.” Me: “How long have you been in NY? Do you like it?” Her: “A few years. It’s okay?” Me:“What do you do?” Her: “Work in Finance.” Me: “Do you like it?” Her: “Yeah” Me: “Okay do you mind if I ask you a weird question? If you could choose between flying and being invisible which would you choose?” Her: “Huh? I don’t know.” Okay that last part is a little exaggerated, but you get the point. First dates are awkward but you know nothing about each other so all you have to do is be able to talk about yourself and ask a few questions. If you just engage a little I find more interesting conversation happens on its own. If you refuse to use more than four word answers then you are both fucked.
What do you usually wear on a first date?
I wear what I would wear out to dinner with friends. Jeans, a nice top and fun shoes. I also usually up my make-up game for dates. I am relatively femme and I tend to like girls who are even more femme then I am.
Tell me about the weirdest or worst first date you’ve had with someone you met online…
The weirdest was definitely the stand-up comedy show I mentioned last time. The worst was this girl whose best girlfriend’s friends has just gotten engaged. She told me about it right away and I quickly got the feeling she was very upset by this engagement and had serious feelings for one of the girls. She was distracted the entire time and both of us just wanted to get out of there as quickly as possible. Shit happens, but if you have some drama going on then re-fucking-schedule.
In your experience, do the people you meet look like their profile pictures?
When I was dating guys I always thought they paled in comparison to their pictures, but the ladies tend to look better than their pictures. Either guys are blinded by self-confidence while ladies tend to curb expectations. Oooooor I’m just uninterested in the reality of dating a man and very interested in the reality of dating a woman.
