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Last week, I talked about some general dating fashion tips, but this week, let’s get specific. How do you know what kind of date calls for what kind outfit? Check out the list below for some guidance:

Coffee date: Asking someone for coffee means “you’re a decent online conversationalist, and I’m ready to meet you in person, but I’m not willing to commit to anything involving time or money in case we don’t click in real life.” Due to the casual and brief nature of the coffee date, you’re allowed to look casual. However, because of the brief encounter, your first impression is even more important here. This means that you should take care to look good and presentable, even if you’re wearing casual clothes. Do not wear gym clothes, leggings, or anything that shows you clearly stopped by the date on the way from an activity that involves sweating.  A sundress, jeans, or a sweater dress and boots in the winter is perfect.

Drinks and/or dinner: I put drinks and dinner in the same category, because, if a drink date goes well, it will often lead to dinner.  Assuming this dinner date doesn’t involve a drive-thru window, look extra nice!  Ladies, this means a dress and heels (unless your date is shorter than you, in which case, use your discretion), or something equally dressy. Guys, slacks and a shirt always work – and tuck it in and use a belt!

An “activity” date: This can include bowling, hiking, rock climbing, or any extreme adventure from The Bachelor that doesn’t actually happen in real life.  You will be moving around, so you want to be comfortable (i.e., not pulling up your strapless bra or tugging at your dress), but this is NOT an excuse to wear some ratty old gym clothes.  ‘Athleisure’ is a thing for a reason.  Leggings (in good condition) plus a bright colored top and tennis shoes will do for the ladies.  Guys, clean clothes without holes and tennis shoes in good condition are acceptable. You might decide to go to a casual restaurant afterward, so make sure your outfit is versatile.

Wild card: In this scenario, all you know is that you’re getting picked up at 8. You aren’t sure where you are going or what you’ll be doing.  Unfortunately, you must be prepared for a multitude of situations.  You should be safe wearing something on a level between your coffee date and dinner date.  Wear semi-comfortable shoes in case you end up walking more than expected, and for either gender, you can’t go wrong with nice jeans and a cool jacket.

OK, you’ve nailed down a date. Nice work! Now, time to panic: what should you wear?  Selecting an outfit can be stressful – especially when you are meeting someone for the first time and want to make a good impression.  To start picking out a date look, ask yourself a few questions:

• What is my personal style? What types of things do I typically wear?  A first date is not necessarily the best time to try out a denim jumpsuit to see if you like it.
• Who is my date? A grad student?  A lawyer? A single dad? This doesn’t necessarily determine your date’s style, but it can provide a hint as to his level of formality.
• Where are we going? If you aren’t familiar with the place, do a little research.  Websites usually have photos and reviews where you can get a good idea of the vibe.

As much as we like to think that a date is only evaluating your personality, that’s just not realistic.   The truth is that your date is 78% more likely to ask you on a second date if he likes the way you look.  OK, I made up that statistic, but your appearance IS a very important factor in determining whether or not you will get another chance.  If you and your date are evaluating each other as potential soulmates, mutual attraction is one of the first things you’ll both notice.

A few general Dos and Don’ts about what to wear:

Do express your personal style but don’t dress in an extreme way.  Especially if you have never met before in person, you don’t want to embarrass your date by sporting something generally considered odd, like a tutu over jeans, or coat and scarf when it’s 90 degrees outside.  Also be weary of something super cool and trendy that may not be well understood by the opposite sex (harem pants, anyone?).

Do err on the side of being overdressed rather than underdressed.  You want your date to know that you value the time you are spending together and that put effort into getting ready!

Don’t wear anything too revealing. Yes, it’s a date, and yes, you want to look good, but don’t display all your goods. Keep things in proportion by highlighting one body part – so if you wear a short dress, pair it with long sleeves or a high neck, and sleeveless tops work well with longer and bottoms.

Guys – you aren’t off the hook here.  A first impression might even be MORE important for you, as girls (whether we like to admit it or not) tend to be more judgmental.  Although there aren’t as many rules for men, it’s important to look polished!  At a minimum, you should shower, shave, and comb your hair.  No one is impressed that you came straight from the gym.  Most date attire for men boils down to the skill of picking a combination of a shirt (polo/button down/sweater), pants (jeans or khakis), and shoes (no tennis shoes) that don’t horribly clash.  If you want bonus points, tuck in your shirt. Avoid cargo pants, and make sure your socks match your shoes.

Readers – what do you think?

PS – special thanks to JA, my sister/aspiring stylist for her help with this post!

Read Part II of this Post Here >>

“Can I come in for a nightcap?” *Panic*  This question is a variation on “want to come back to my place?” and no more polarizing post-date words have ever been spoken. But, not for the reasons you might think. Inviting someone back to your place unexpectedly is a terrorizing thought to… someone who has a messy house!

Single people, i.e., people who are dating and might find themselves in such a situation, tend to live either alone, with a roommate or two, or with their kids, all of which are risk factors for living in filth. It’s pretty easy for me to go days without putting anything (including dishes or clothes) away, and this slothfulness was only compounded when I lived with roommates in the past.  So what to do if a new dating partner stops by or wants to come over without advance notice?

My dad always said, “How will you get a guy if your apartment is such a mess? What if he wants to come over? What kind of housekeeper will he think you are?” You know, something, Dad?  I think you are right.

Some housekeeping disasters just can’t be explained away, so your best bet is strictly preventative.  Improve your own life AND your likelihood of impressing a date by always keeping your pad in showable condition.

If you can’t bear to vacuum and dust everyday, here are the basics:

1. Keep your bathroom presentable. Let’s say a guy is dropping you off at the end of an otherwise decent date, and he asks if he can come in to use the bathroom.  Because you were just getting ready for a date, there’s a good chance your bathroom looks like Sephora exploded on your counter, leaving a trail of strewn about hair sprays, eye shadow palletes, hot rollers, etc. all over the place.  Next time, when you are finished in the bathroom, throw all your products in a basket, get rid of stray hairs that always find their way into the sink, and put the toilet paper roll back on the holder, just in case!
2. Always have a clean entryway or living room. If someone walks you in to your place, this is the first impression he or she will have. When you are getting ready to leave, take 5 minutes and move your mail, purses, shoes, and mountains of outfits that you tried on and didn’t wear and shove them into a closet.  Just don’t forget where you stash your stuff. This is frustrating. Ask me how I know.
3. Make sure your kitchen isn’t gross.  If someone stops by or comes over, you will probably offer a drink.  Don’t be that person who can’t find a clean glass among a sink full of dirty dishes. Oh, and try to keep a hand towel for guests in the kitchen and bathroom too.

They say an ounce of prevention is worth a pound of cure, and when it comes to cleaning, a little bit of straightening up is worth it to prevent potential embarrassment!

Somehow in my mind, shopping for a new watch is equated with shopping for a husband.  Allow me to explain this thought process through a journey to the center of my mind: I’ve always been a watch person – I feel naked without one, and I’ve worn several different timepieces throughout my adult years.  And I tend to be more of a “quantity over quality” watch owner, preferring lower quality, trendier  pieces to classic expensive timepieces that will last forever.  A consequence of this habit is frequent replacing – straps break, batteries fail, faces tarnish, and in one case, this chain attached to the strap that I thought was really cool just plain fell off. My penchant for replaceable (read: cheap) watches means I’m always on the lookout for the next style I might want to wear. So whenever I’m shopping at a department store (or let’s be honest – Marshalls and/or TJ Maxx), I usually peruse the watch section so that when my current watch inevitably breaks, I’ll have a replacement in mind. One store in particular usually has a ton of good options for sale, and I never have trouble finding several that I like when I shop.

So anyway, a couple weeks ago, my watch battery died, and soon after, I realized that water droplets had somehow snuck under the glass that protected the face of my watch, rendering it unreadable.  The situation wasn’t worth fixing, so I headed to my favorite store to find a replacement.  But something different happened. Now that I actually had to pick one to buy and wear everyday on my wrist, I suddenly couldn’t find one that I liked! Just a few weeks prior, when I wasn’t seriously in the market for a watch, I saw a display of nice watches, any one of which would look nice and have the features I wanted.  But now that I actually had to choose one to wear, all I saw were flaws.  This one was fine, but I really wanted a leather wrap-around band and this wasn’t exactly what I pictured.  And that one had a nice face, but the band was a rose-gold color that clashed with my other jewelry.  This inner dialogue went on and on until I couldn’t find a single watch that met my expectations. So I left the store, defeated.

And then, standing there empty-handed in the mall parking lot, I had a mini-epiphany: This is exactly why I leave so many dates “empty handed.” The same psychological principle is at play here.  When I look at a group of something (watches, people, whatever), I see a general sense of possibility – a pool of potential. But selecting one out of the group means leaving other (possibly better) options behind, or picking the one that will turn out to be a lemon, or deciding that one is best, only to have your tastes change shortly after selection.  A watch is just an object, and especially for me, it’s not a permanent life fixture. So if I felt that way about my watch selection, it’s no wonder these thoughts and the related fear cause me to “leave the store” of dating without selecting an option.

So back to the story – there I was, watchless. I decided to go to a different store and check out the selection, and I found the same issue – lots of choice, none perfect. It was getting late (I think – I didn’t know what time it was) and I didn’t want to go home empty handed. So I picked the least objectionable option and called it a day. And you know what? I’m really happy with my reliable new watch. I now like the way it looks, and it runs great.  A stylish coworker even complimented it.

So the next time I find myself surrounded by options of people, yet feeling disappointed and ready to leave, I hope I remember to glance at my watch – it will tell me that it’s time to change my thinking.

Have you ever realized how many famous adages or proverbs actually contradict one another? Within the last two blog posts, I advised you to be less picky when dating, yet not settle. Don’t discount people too quickly, I said, yet don’t force a connection if it’s not there.  All of this sounds like reasonable advice. But, which is it?  You can’t have it both ways, right? I guess the good news with conflicting information is that you really can’t go wrong either way, since someone says it’s right. This got me thinking about other instances of paradoxical advice – they are more common than you might realize! Which of the examples below is your favorite?

• Absence makes the heart grow fonder vs. Out of sight, out of mind
  • Favorite sayings of long-distance romances everywhere, these two basically provide opposing advice. There have been different times in my life when both of these have been true in different situations, but you might as well focus on whichever you want to be true, because they cancel each other out.
• Love yourself as you are vs. Always strive to improve
  • The essence of this contradiction is often found in women’s magazines – the messages “love your body!” and “you’re beautiful the way you are!” sound great until they are sandwiched between articles on how to lose 10 pounds in a month and how to get guys to like you by changing your hair and makeup. But these are not mutually exclusive – it’s possible to love yourself and want to improve, both internally and externally.
• Play hard to get vs. Don’t play games
  • Ah, the classic debate – do you try to play it cool by calculating how often and how long to wait before responding to someone, or do you just do and say whatever you feel like doing and saying? Opinions vary and often conflict, as does conventional wisdom. Looks like the jury’s still out on this one.
• Birds of a feather flock together vs. Opposites attract
  • I hear both of these sayings all the time – could it be that they are both true, to some degree? Maybe we tend to flock together with people who have similar interests, goals, background, and values. But an opposite temperament or personality brings a little spice to life.

The moral of the story is that no dating advice is ALWAYS true in ALL situations. So be judicious when taking well-intended dating advice from people who don’t know your particular situation. But also remember that wise men think alike… but fools seldom differ.

Last week, I talked a bit about how you should give more matches a chance. Just because you’ve seen and ignored the same tired profiles over and over again in your zip code doesn’t mean that they aren’t a good match for you!  This is true. However, I tend to play devil’s advocate quite a bit (with myself) and was thinking: why date people you aren’t interested in just because they are available?  I might only find a dozen young men in my area who are my age, but what if I don’t want to date any of them? Should everyone in the same zip code just pair off with another person they find the least intolerable? Is that how marriage works?

I’ve come to the conclusion recently that some people are just naturally more picky, or, excuse me, selectively-inclined, than others. And this is fine. If we all dated like Jerry Seinfeld, no one would ever get married, family structure could break down entirely, and we’d all end up alone eating lots of cereal. But if everyone were forced to just “pick someone,” many people, though not necessarily all, would be miserable. If someone has found a happy medium between these extremes, please inform me what it looks like.

How do you know if you’re too picky? I’ve definitely been accused of having an overly healthy degree of selectivity. There are likely several reasons for this, none of which I’ll describe here, because honestly, I’m not sure what they are. But am I being too picky when I reject an offer to be set up with the cousin of someone’s neighbor who is 20 years my senior, lives in another country, and just finalized his divorce?  I say no. Mrs. Goldberg at shul might say otherwise. But I’m holding my ground. I mean, you see how picky I am about my shoes, and they only go on my feet.

In my opinion, there’s no need to go out with someone out of pity, convenience, spite, revenge, or obligation. If you aren’t interested or don’t see the possibility of potential, it’s okay to pass. If you’re feeling that resistant toward meeting someone, it’s much more likely that you’ll feel resentful or act rudely than feel surprisingly delighted after meeting him or her. Feeling neutral is one thing – if you don’t know someone or feel on the fence, by all means – it’s just a date – go! But feeling repulsed by a photo, getting in an email argument over opposing views of the world, or even a strong negative gut feeling – these all warrant some selectivity.

Those examples might be pretty straightforward, but what if you don’t want to date someone because one of her nostrils is a little bigger than the other, or because he won’t let his food touch on the plate? Or because she didn’t go to an Ivy League school, or his glasses are out of style? This is where pickiness gets interesting. There can be a fine line between appropriate selectivity and self-sabotage, so give people the benefit of the doubt, but trust your gut.  There’s a lot more to say about this topic — stay tuned for a future related post. In the meantime, in honor of the 20^th anniversary of Clueless this month, I’m Audi!

“100hookup? Yeah, no one’s on that.” “I’ve tried it, but there’s no one on there.”

Have you ever heard someone say this before? I know I have. Heck, I’ve probably even said it before. But you know what? Unless you live in Antarctica, there ARE people on there. In fact, in preparation for this article, I searched in several different cities to find one with “literally no one on there,” and it was tough. Shout out to the 100hookuprs in Anchorage, Alaska; Cheyenne, Wyoming; and Bozeman, Montana!

I admit that for folks in these kinds of cities, local dating may present some challenges. And as someone even in a mid-sized Midwestern city, I can attest that sometimes the options feel… limited.  But, there usually aren’t zero options.  It can be quite discouraging to scroll through the “same old faces” and not see anyone who interests you. I get it.  And I totally understand why you might ignore the outdated profiles that have been cycling through your matches since the Bush administration. If you’ve used 100hookup for a little while, unfortunately it’s not hard for other “long termers” to become invisible! But I encourage you to take a second look. It’s possible that someone’s cover photo is unflattering, yet their essay reveals a more telling portrait of who he really is. Or maybe you exchanged a few messages with someone a couple years back, but now you’re curious if she still might be interested.  Regardless of why you may have skipped over or subconsciously ignored certain profiles, remember – we are all on the same site presumably looking for the same thing. Give people a chance – there is no obligation to buy!

Conversely, if you haven’t updated your photos or essays in a long time, or if you’ve changed something about yourself, it’s time to update your profile.  I know my eye goes straight to those little “updated” tags – it’s like a new and improved symbol.  A couple times I’ve even wondered who a new cute guy is only to realize that he’s the same person I had previously overlooked – just with an updated photo.

Your online presence is like your house or car – it requires a little bit of regular maintenance to keep it working effectively.  So unless you live in the Arctic Circle or a similarly populated place, it’s unlikely that there’s no one on 100hookup – just maybe no one who takes the time to regularly update and enhance their profile!  So mark your calendars: change your oil every 3,000 miles and update your profile and/or photo to keep everything in good working order.

My birthday was last week.  This is exciting only because it means I got to identify the most random Facebook wall-writer of the day. That’s a funny thing about birthdays in this era: it’s the one day a year you hear from people you barely know — your preschool bestie, someone you met once eight years ago on vacation, your old roommate’s cousin, a great aunt who is new to Facebook and now invites you to play Candy Crush every day, and sometimes even strangers. This year, someone I don’t know even enthusiastically wished me happy birthday on my wall! Conversely, I have friends I see regularly who don’t really acknowledge birthdays — it’s just not a big deal.  In some friendships, we’ve established an unspoken rule that we don’t exchange birthday gifts or really acknowledge the day. And that’s fine with me — no one gets mad — that’s just how it is.

My point is that there’s a lot of variability in how people acknowledge and celebrate birthdays. So how are you supposed to know if and how to acknowledge the special day of a brand new significant other? If you just started to date someone new, do you even mention your birthday? What if you don’t know if you’re exclusive yet — does it matter? What if you get him a birthday gift, but he doesn’t want to go out with you on his actual birthday? Is a surprise party out of the question? To avoid all these issues, you should probably plan to break up with this person right before either of your birthdays is approaching. You can get back together afterwards.

Kidding aside, this can be a tricky occurrence. So I’d recommend being honest and taking cues from the other person. If you’re a cake, ice cream, and presents-kind-of-person, say so! Assuming you’ve been out more than a couple times together, it can’t hurt to mention that your birthday is coming up and express your expectations.  Unless your expectations involve extravagant gifts or selfish demands. Then it could hurt.

However, if you like this new person, and you want her to be part of your birthday, invite them along to whatever you have planned.  If you’d rather spend your birthday solo, curled up with a book, that’s cool too!  Just tell your new significant other, so he or she doesn’t try to plan a surprise party.  And if you’re expecting a big deal, don’t say it doesn’t matter how you spend your birthday, because you’ll only wind up disappointed.  And don’t be offended if your new beau or lady excludes you from birthday plans — it could be that there were no plans at all, or they might want to do something really low-key with close family.

Oh, and a final note: if you do have a date on your birthday, please wear something other than your birthday suit!

There comes a pivotal moment while waiting for a date to arrive at which point you have to make the official call: you’ve been stood up. This moment differs from person to person – some people might give up after waiting fifteen minutes, others thirty, or even an hour for some.  Or you may be in the George Costanza camp and wait about five minutes, after which you eagerly go home, change clothes, order food, and bask in the glory of eating dinner in front of the TV in your underwear. (Wasn’t it George who said something like, “I never met an obligation I was upset to get out of!”?)

No matter your personal tolerance for tardiness, being stood up is no fun. But, how do you determine if someone is just really late, or if there is a legitimate emergency, or if they just aren’t coming at all? If you’re the one running late, how far in advance do you inform your date? If one party is running really late, at what point do you decide to just cancel or reschedule? If someone has a good excuse for being late or not showing up, do you give him/her another chance? As usual, I offer more questions than answers. However, here are some general guidelines:

• I generally give people a ten-minute leeway without question, but I tend to run on the late side myself, so your tolerance may vary.
• If you are going to be more than a few minutes late, inform the person who is waiting for you and apologize when you arrive.
• If you’re waiting on someone who is 5-10 minutes late, try not to make a big fuss about his/her unpunctuality on the first date. Stuff happens – be forgiving. But if it happens continuously and it bothers you, speak up!
• If you are going to be 20 or more minutes late, you better have a decent excuse (or make one up). Call your date, explain, and offer to reschedule if he or she prefers.
• If you’re waiting on someone who is significantly late, call and/or text to make sure you correctly communicated the same date, time, and location. It’s definitely possible that one of you showed up at a different location of the same place, for example.
• Waiting on someone longer than 20 minutes consistently? Possible grounds for dismissal.
• In the event that you get a better offer on the day of the date (or on the way to) and you decide to ditch your plans altogether, please inform your date. Say something came up. I suspect that this happened to me once – I was waiting for a guy to pick me up, and he never showed. After texting and giving him a ring, I got no response and never heard from him again! But don’t worry about his well-being – I could see that he was regularly logging in online and even updated his profile photos not long after that night. Harrumph.

Anyway, the point is: be considerate of people’s time. If someone isn’t considerate of yours, proceed with caution. And if you’re completely stood up? At least you can always spend the evening with an awesome, good-looking person, i.e., yourself.

The world is split between two kinds of people: those who run toward an acquaintance at the grocery store, eager to say hello, and those who dart away and hide in the next aisle in an effort to avoid forced small talk.  Which kind of person are you?

Do you fall into the same camp if the acquaintance is someone you previously dated? What if you recognize someone with whom you’ve previously changed messages, but you never met in person? What if the other person doesn’t recognize you? What’s the protocol here?

Relax, dear readers, I’ve got the rules below.

First, as a natural hider, let me say that avoidance is always an acceptable option.  On days where I just don’t feel like talking to someone, or I’m in work-out clothes with post-gym hair, or whatever, I’ve been known to feign interest in the nutrition facts of Worchester sauce until the perceived social threat has passed.  However, once you commit to the avoidance tactic, what would have been a 10-minute run to the store can easily turn into a tactical strategy of hard-core hide and seek.  Be forewarned.

But once eye contact has been established with the acquaintance, things get a little trickier.  Proceed as indicated below:

If you recognize someone who…

• Is on 100hookup and you might be interested: Smile and make eye contact
• Is on 100hookup and you are probably not interested: Avoid or smile weakly
• You recently exchanged messages with: Smile and make eye contact
• You exchanged messages over 6 months ago but never met: Avoid or smile, depending on whether you are still interested
• You went out with once or twice: Smile
• You went out with on the worst date of your life: Avoid — or, if you’re in a movie, make a loud scene resulting in the destruction of a pyramid of produce, causing innocent bystanders to start tripping over oranges
• You dated for a few months: Smile and wave politely, depending on how things ended
• You dated for a substantial amount of time: This really depends on the nature of your relationships, but given its length, you will know what feels most comfortable
• Is a random, cute stranger: Smile! And ask for a food recommendation  – why not?

If you’re ever unsure whether to approach someone whose relationship isn’t listed above, come find me for consultation – I’ll be the one hiding behind giant sunglasses pretending to inspect the melons really closely.