18 Real Online Dating Lessons I Learned the Hard Way

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Online Dating Tips For Women

When my marriage ended after eighteen years, I found myself tossed back into the dating pool. Not an easy task for a fortysomething female. To put it in the nicest terms possible, the relationships that followed weren’t, um, noteworthy. The straw that broke this camel’s back was the boyfriend that lied about his entire life and got arrested for shoplifting just before Christmas. That’s when I decided to take my pathetic ass online to find a man.

Little did I know, online dating isn’t as straight forward as it seems. Many lessons have been learned on this girl’s quest to find the perfect man. To make your life easier, I’m going give you some online dating advice; lessons I learned the hard way.

While You’re At The Dating Site

1. Don’t lie (or stretch the truth…too much)

Don’t create a profile in which you are more attractive, fun, successful and adventurous than you really are. Definitely don’t lie about your children or your age. Why? Because if you find a man made of relationship material, you will eventually have to fess up.

Keeping lies dangling between you and your new guy is not a good way to begin a love connection. Lying is a big deal and some people take it very seriously. Even a small lie might seem big to someone who put their trust in you.

2. You don’t have to respond to every message.

It’s chaotic. Even just saying, “Hey thanks for the message, but I’m not interested,” becomes time consuming if you’re responding to a few men a day. Take your time and be choosy. When I receive messages in my inbox, I read the prospective date’s profile. If I’m still interested after that, then I respond.

I also never respond to messages such as, “Hi beautiful,” “Hey baby,” other one liners, or date requests before a written exchange. My mantra: if you’ve not read my profile, I’ll not respond. I ended up putting a disclaimer on my profile stating that I would not write back if I was not interested.

3. Only instant message if you have no life.

I mean, it’s not an earth shattering mistake, but there are always people who have nothing better to do all day than send you messages. This is annoying. Also, something that starts out innocently enough may very quickly turn uncomfortable in a gross, repulsive, or perverted manner. Chatters can easily get butt hurt if you don’t immediately respond to them. Rather than taking chances that someone on the other end of that IM will actually be interesting, it’s just easier to disable instant messaging on all dating accounts.

4. The block button: use it.

If you feel harassed, receive unsolicited disgusting message, (yes, it happens; some men are pigs) or find yourself the obsession of a creep or clinger (I explain this later), block them. That button is there for your safety and sanity. Also, don’t hesitate to report the admirer if they go above and beyond disturbing, scary, or perverse. The online dating scene would be better off without them.

5. Don’t be judgy.

I suggest not using the “yes” “no” or “maybe,” aspect of any site (unless you’re on Tinder, then you don’t have a choice. I loathe Tinder specifically for that reason). This feature has you judging a book by its cover, which I think is crappy. Think about it this way–do you want to be on the other end of that superficial assessment?

6. Don’t be a date hoarder.

What I mean is don’t set too many dates. This is a total noob move. You do not need to date all the men. You’re not in a race or competition. Take your time. I remember having four dates in one week and it was crazy-making. The men aren’t going anywhere. Believe me. I’ve seen some of the same men on these sites for more than three years, which seems pathetic, but many of them are just like you and me, kissing a lot of frogs until they find their prince(ss). One at a time girls. One at a time.

7. Be curious.

Get any misconceptions and/or dissimilarities out of the way by asking questions. If the guy doesn’t want to answer? Red flag. I’ve found the following important topics for discussion:

Children: For example, I will not date men with young children. If they say they have no children or they are all over eighteen, yet have a small child on their profile, question it. One man I was texting stated on his profile that all his children were over eighteen. When I found out he also had a five year old, I felt duped and told him so. So not cool. He became defensive. That relationship didn’t work out so well. Knowing the kid situation in advance can save a lot of headaches.

Pets: Are you an animal lover? Hater? Do you have allergies? If you answered yes to any of these questions, get the skinny on your date’s view on animals. If you hate pets or you have allergies, you probably don’t want to date a guy that sleeps with his dog. Just sayin’.

Work: In my experience, many men on dating sites are extremely vague about their work situation. Sales could mean telemarketing. Self-employed could mean unemployed (so could landscaper, painter and other odd jobs, or they could be totally legit). You get the picture.

Profile pics: How recent are his pictures? Who are the children in the photos? You wear a hat in all your photos, are you bald? You’re not in any of your photos, is there a reason for that

Activities: If you’re a couch potato, you probably don’t want to be dating a gym zealot and vice versa. If you have that weird skin disease which doesn’t allow you to be in sunlight, you should probably stay away from a beach bum. Find out about hobbies and interests to see if they are compatible with yours, out of the question, or, well, deadly.

When your heart is on the line, you need answers. I think these are all valid questions.

If you make this questioning process sound more like genuine interest and less like the Spanish Inquisition, it shouldn’t raise any red flags on his end about you being a crazy stalker person.

8. Don’t get personal too soon.

Giving out personal information while messaging with someone is a bad idea. This includes your phone number. There’s no rush to move from messaging on the dating site to texting. Only give your number out when you’re comfortable with the person on the other end. Don’t let anyone pressure or bully you into it. Also, experience has proven that giving your number out is an invitation for some men to send a dick pic. If you’re into that kind of thing, enjoy. However, if you prefer that your cell phone stays free of uninvited stranger’s penises, you might want to take your time when sharing your number. Better safe than a phone full of dick.

9. Never ever video chat.

I should have known better. I’m not that naïve. A guy began video chatting me one night on Plenty of Fish. He was attractive and funny; we were having a lovely conversation–until he excused himself to leave the room. That’s when I found out that beyond the video frame he was buck naked. I was astonished and somewhat amused that he had the balls (no pun intended) to go there. I blocked him. I was there to meet guys, not watch porn.

Once You Make It On The Date

10. Be involved, be organic.

Make sure you are an active participant in the first date planning process. Don’t take the chance of having to bungee jump if you’re afraid of heights, or death for that matter. Also, be yourself. If you love to eat, don’t starve yourself by ordering a side salad. Keep in mind, comfort is more important than style. Don’t wear stilettos if you prefer flip-flops or a dress if you prefer pants. You will look like an idiot if you are constantly adjusting your clothing or stumbling with every step you take.

11. Let him down.

If you’re not feeling a connection, do both of you a favor and be honest. Thank them for the date, then tell them you’re just not that into him (but nicer). Don’t ignore him forever hoping he goes away. That’s hurtful and a waste of everyone’s time. And honestly, some men don’t get the hint.

12. Sobriety is your friend.

Being a drunk hot mess is not a good idea on a first date. In fact, it’s pretty much embarrassing and repulsive. You’re also contributing to your own self demise, especially if you’re on a date with the kind of man mentioned in #13. Don’t let him take advantage of your drunk ass. Keep it clean. Keep the alcohol in moderation.

13. No first date cuddle time.

Don’t go home with him on the first date under any circumstances. I did this under the guise of watching a movie. I felt comfortable doing so because we had talked a long time about everything and he seemed very sweet and genuine. Can you say gullible?

Once we got into his house he pounced like a tiger in heat, which apparently was close to the truth since he said he hadn’t had sex in three years. Insanity. I informed him that under no circumstances would I be the one to break his losing streak. Then *poof* I was gone. Never again. Ladies, you need to realize and remember that some men are on those sites purely to get laid.

14. No f*%cking on the first date.

I’m not saying this is always a bad thing, I mean, it is 2015. In my opinion, sex on the first online date is taboo. Stranger danger. You know next to nothing about the person across the table from you. He may be charming, attractive, funny and intelligent, but you have all the time in the world to screw him. If he’s into you, he’ll wait for it. Seriously, be classy. Keep your legs closed.

Post Date

15. Screw the three day rule.

Meaning, if you like the guy, for God’s sake call or text. Don’t wait until three days have passed. That practice is immature, stupid, and archaic. In this day and age, with technology resulting in immediate gratification and shorter attention spans, nothing waits. Wait three days and you might miss your window of opportunity with your Mr. Right.

16. Don’t be a clinger.

Do not follow your new man around like a puppy. Do not make him your everything. Never forsake your friends for a relationship. You will look pathetic and docile and your friends will drop one by one. Being clingy isn’t cute, charming, or sweet. It’s pathetic and annoying. In fact, you could annoy yourself right out of that relationship.

17. Never, ever grovel.

When a man breaks up with you (or simply just isn’t that into you), never beg for a second chance. I thankfully did not do this, but someone did it to me. If you get rejected, take it like a woman. Keep your chin up and back away from the man with your dignity intact. Groveling is a huge turn off and in all honestly, kind of creepy.

18. Do not drunk dial (or text).

Yes, I made this mistake. Once. Painstakingly, it was with a guy that I really liked. I realized what I was doing, so continued to text in order to apologize and save face. Then I realized how many times I’d texted, so I kept texting to explain that I really wasn’t a crazy person, which made me look like, you guessed it, a crazy person. Needless to say, he stopped seeing me.

It’s not easy to find Mr. Right, especially at a *cough* seasoned age. If this is your first time plunging into the online dating pool, I wish you every success. Making initial mistakes and then adjusting accordingly made my online dating experience significantly smoother. Not as many bad dates, no longer exposed to the pervs of the online dating world, and no more looking like an idiot. I have learned from my online dating mistakes, and I hope you can too.

Have you learned any hard lessons while dating online? Do you have advice for others taking the plunge? Feel free to share them in the comments. We need to stick together and help each other along this crazy adventure of finding Mr. Right.

Struggling with online dating?  Check out this video where Michael Fiore which explains exactly what your online dating profile says to men. Go watch it now.

online dating video

Megan Bostic

About Megan Bostic

Megan Bostic has an unhealthy obsession with sock monkeys and lives in the rainy but lovely Pacific Northwest with her two crazy beautiful girls. She’s the author of the Young Adult titles Never Eighteen and Dissected. You can find her on Facebook, Twitter, a variety of online dating sites and anywhere else social media addicts hang out.

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