Tips on Dating Men vs. Dating Women

Dear Papabear,

As I've told you in the past, I'm bisexual.

I'm going to be graduating in June, and after that, I would like to start looking for a boyfriend. I'm not about a superficial, casual fling. I'm talking about a long term, committed relationship in which I feel a legitimate connection. 

You see, I've only dated girls up to this point. I have zero experience dating other guys. Do you have any general advice for dating men?

Hugs, Anonymous (age 18)

P.S. Does anal sex hurt?

* * *

Hi, Anonymous,

I hear this sort of thing a lot from writers: “I’m looking for a boy/girlfriend.” I, personally, don’t care for the hunting strategy. For one thing, it kind of makes you look desperate, which is not very appealing to most potential mates. For another, it might make you rush into someone’s arms too quickly just because they gave you a hint they might be interested. On the other paw, supposedly matchmaking services do quite well (although there have been reported cases of unhappy customers having dates from hell), or, if you have a lot of money, you can hire a personal matchmaker for a much more individualized experience.

My recommendation has always been to abandon the computer algorithms and go for something more organic. That is, go out and experience life, develop hobbies and interests and activities that expose you to connecting with other people with like interests, and you will be much more likely to find someone suited to you. Not only that, but since you are meeting them in person, there is none of that long-distance crap that dooms most such relationships to failure.

So, the big question: dating boys versus girls. You’re asking the right furry because I’ve done both. The thing you have to be careful about with men is that they tend to be a lot more libidinous than women (pardons to readers for gross generalizations, but the writer asked for general advice so I’m giving some generalities that I know are not always true but often are). So, when dating a guy, you want to make sure that he’s not just looking for a hook-up and/or operates on a deeper level than whether or not he finds you physically attractive.

On a completely biological level that I acknowledge as extremely shallow (taking out all other factors that make us much more than just breeding machines), women are seeking men who will be stable and good providers for their children (obviously not true when talking about older people seeking companionship, but you’re 18 so that’s not relevant), so the tendency is to look for someone with a good income and stable job who is also healthy. Biologically speaking, health is often marked by regular, symmetrical features and a fit body (there’ve been studies on this at the university level that show this to be true), which is why both women and men go for these features that we deem “handsome” or “pretty.” Men look for features indicating a woman who will be able to bear and nurture children, which is why curvy hips (good birth canal) and large breasts (ample milk) are attractive to men.

Some people are more ruled by their biological urges than others, and these are the people you wish to avoid because they make for shallow, unpleasant relationships if all they care about is the physical and monetary.

Putting all that aside, the difference between dating a man and dating a woman is that it is quite true that women are from Venus and men are from Mars. How you deal with this depends on what kind of person you are and what type of person the woman is. There are effeminate men and manly men, as well as butch women and girly girls. There are also mixes of the two. It’s usually a better match to link like with like. For instance, my marriage worked rather well because my ex had both masculine and feminine sides (she loved cars and sports and was [and is] a strong woman and I liked that, but she also had a feminine side and so did I, so it worked well). The whole reason I didn’t think I was gay for the longest time was that I do not care for effeminate men (case in point: walking to a restaurant last night Yogi and I came across two swishy men who walked with limp wrists and giggled; I cringed), but then I found bears and that worked well for me.

I guess this is a long-winded way of saying that when dating men you should seek guys whose balance of masculinity/femininity is in tune with your own, and you should seek someone who isn’t just into you for your looks. And, OMG, guess what? It’s the same for when you are dating women. Just as you would hope that they wouldn’t be shallow, don’t be shallow yourself. Just as you would hope they would be kind and considerate, be kind and considerate to them. Because, male or female, we’re all human beings and expect the same treatment.

Okay, now to your last question. (Sensitive readers who are easily offended, you might want to stop reading this now and go read a letter in the Papabear archives because I’m going to be as frank or more so than Dr. Ruth Westheimer ever was. If your first reaction to this is “Eww,” stop reading now). 

Does anal sex hurt? Not if it’s done right. If it hurt, no one would want to do it LOL. Presenting . . . 

Papabear’s 7 Tips for Satisfying Anal Sex

1) It is unpleasant to make love to a guy who is not clean. Make sure you clean yourself out well, and this means a good flushing (bottle enema such as that made by Fleet are good, but even better is one for the shower). Clean yourself inside and out thoroughly.

2) Lubricant. It will probably take some time to find one you like (Gun Oil is good IMO), and also to learn that while too little is not good, too much also makes the experience a bit too slip-and-slide. For added comfort, heat up the lubricant in a bowl of hot (not boiling) water. Nothing can chill the moment more than cold lube.

3) CONDOMS, CONDOMS, CONDOMS. Oh, and did I mention CONDOMS? 

4) If you are a virgin (and even if you are not), you might want to experiment a bit with toys at first. This might sound odd, but everyone has slightly different plumbing—meaning, the way your insides are constructed, how wide or narrow, even where the “curves” are. Get to know your insides and you will learn what positions work best for you—on your back, doggy style, on your side, or riding on the lap. 

5) When on the receiving end, have your lover begin slowly so you can get used to him before going for the all-out humping :P. As for those on the giving side, you are not a jack hammer stuck on the fast setting. Learn to vary speeds, depth, etc. for a much more erotic experience for both of you. The most sensitive tissues are at the threshold of the doorway, not the basement.

6) Speaking of skill, you might want to have your first experience with someone who is not a virgin and knows what he is doing. There is, IMO, nothing more awkward and uncomfortable than two virgins going at it. You want your first experience to be a good one. 

7) Communicate with your lover; don’t be afraid to tell him what you do and do not enjoy and ask him to share with you, as well.

Bonus Tip: Did I mention CONDOMS?

Good luck!

Papabear