99 Problems: Texting Issues, Cuffing Season Catastrophes, and Girlfriends Who "Get Around"

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Ever since I got out of college, I've been having trouble finding and dating women. I'm on a two-month drought and with cuffing season approaching, it looks like I'll be inactive for the season. Am I just too ugly?

—Dirt On My Shoulder

You're suffering a dry spell. it happens. Usually, when you're single against your will, it's a signal you need an attitude adjustment, not a makeover. A woman won't hesitate to date a guy who isn't "traditionally" attractive if he's confident, cool, and interesting. Pouting, obsessing on your bad looks in a vain way—that will make women avoid you. And can you blame them? It's not a woman's job to coddle your self-esteem. It's not anyone's job besides your life coach.

If you don't believe that you're worthy of a woman's attention, you need to take some time off. Think of it as you forcing yourself to be single as opposed to all those conniving women out there, plotting against your desire for a relationship. (Yes, that should sound crazy, because it is.)

Go after what you're truly passionate about, whether it's perfecting your basketball game or taking a class to sharpen your photography skills. Remind yourself why you're a cool dude to know, and it won't be long before the ladies take notice.

How should one deal with a girlfriend who has had numerous sex partners, many who are guys I know personally? It was years ago, but these guys are still around and she used to be known as a hoe. She is about to move back in the area to be around me, and these guys don't know about the relationship we've been having for the past couple of years. I love her, and she hasn't directly done anything to make me think she would cheat on me. But, me being a guy knows how it is when a girl gets around. No matter what she will always be known as a hoe. What should I do? I tried getting over it but these guys have told me stories about my girl and shit she did, which she confirmed. I know it's in the past, but goddamn! 

—Blaming Tammy

Since you've admitted she hasn't given you any reasons to not trust her, this seems less like a trust issue. Seems like you're more concerned about your relationship with your friends, and whatever jokes they may or may not make about you and dating a woman who has enjoyed some casual sex. 

Think back to when you were younger, the mistakes you made, and the less-than-admirable moves you pulled with women. Surely you’ve learned a lot since then, right? Would you want to be judged based on how you used to act? Why hold her to that same standard, then?

You have two choices:

1.)  Get over it. If you genuinely feel she’s changed, and that she's worthy of your trust, get over her "bad" rep. Stop being a coward and tell your friends how you feel about her. In the end, it’s a relationship between you and her, not you, your boys, and her. If you're honest with them, and they still talk shit, they're probably shitty friends.

2.)  Admit you’ll never get over it. Right or wrong, if you see yourself becoming paranoid, possessive, and/or jealous, walk away. It's the right thing to do by her, and it'll ease your quaking mind.

I need advice on how to text a girl. How do I keep her guessing but laughing, and also make her chase me through text, be mysterious?

—What More Can I Say?

Please don't make it your aim to be mysterious. Text messaging, lacking things like, you know, intonation, is complicated enough. Focus on being mysterious and you'll likely come off as crazy, or too aloof, or something else undesirable, in which case she won't know what you want. Fronting will never work in your favor.

Don't try to make her chase you. That's the adult equivalent of throwing rocks at your grade school crush.

Avoid sending mixed signals. Instead, focus on developing a rapport. Keep your text messages as witty and charming as possible. Your aim is to be engaging and appear interested without going overboard. Do not send a text asking why she hasn't responded when only five minutes have passed.

Ultimately, your goal is to make it beyond text messaging to a real in-person date. That's where you'll shine.

I can't seem to get a woman to be attracted to me long-term. What should I do?

—Welcome to Heartbreak

I haven't been on a date with you, so I can't say for sure what it is you're doing to instill commitment-phobia in your dates. But I do know that anytime you see a pattern developing, it's time to get introspective. Ask yourself: What am I doing that could be turning these women off? If they're initially attracted to you, you must be doing something to blow that. Make an honest assessment: Would you date you?

If you rule out something off-the-wall weird, your issue comes down to one of two things: coming off as too interested, or not interested enough. It's possible that women are interested in a relationship with you, but you appear so aloof that they're unsure about how you're feeling. You can do this directly (by playing it too cool and saying things like, "I don't know if I'm ready to settle down") or indirectly (by not taking her on real [sober] dates, not listening to her, or projecting general indifference). 

On the flip side, you might be rushing the relationship by being too clingy and too emotional too fast, which will sets off warning signals in any sane woman's mind. Connections usually develop over time. As you spend more time together, you will gradually put more effort in and the progression will feel natural. Even if your dying to lock down a winter wifey, pulling out all the stops in the first three dates is not the way.

Instead, try letting things just happen. Project your interest, and be confident that the right woman will pick up on it. You're not going to have chemistry with every woman you meet. Be patient.

I looked through my girlfriend's phone without her knowing and saw that she's texting other guys. What should I do?

—So Paranoid

I wish you would have told us more about the nature of these messages. But since you didn't, will cover all possibilities:

If you found texts that indicate she's cheating (i.e., "Last night was amazing. I didn't even know I was capable of multiple orgasms!") or imply an intent to cheat, confront her about your findings. Be aware that you will be attacked for snooping. And you shouldn't be snooping. But, she also shouldn't be cheating. Chances are, this relationship was unhealthy to begin with.

If the texts are just friendly, ask yourself if confronting her is worth exposing yourself as insecure (which you are, if you're looking their your girlfriend's phone without her knowledge).

Respect her privacy and set some boundaries. If you're unable to keep yourself from rifling through her messages, ask yourself, why? Why are you unable to trust her? Is she doing something to make you feel paranoid? Or is there something in you that's causing this?

Talk to her about your feelings but without mentioning that you've gone through her phone. Unless you want to entertain the possibility of her leaving you.